1,2-Cyclic sulfamidates as versatile precursors to thiomorpholines and piperazines

Organic Letters

Volumn 5, Issue 6, 2003, Pages 811-814

  Williams, Andrew J ^a   Chakthong, Suda ^a,c,d   Gray, Diane ^a   Lawrence, Ron M ^b   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c CHULABHORN RESEARCH INSTITUTE   (Thailand)

^d MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; ESTER DERIVATIVE; METHYL GROUP; PIPERAZINE DERIVATIVE; SULFANILAMIDE DERIVATIVE; THIOGLYCOLIC ACID DERIVATIVE; THIOMORPHOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRECURSOR; SYNTHESIS;

EID: 0141627559     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027418h     Document Type: Article

References (53)

1. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180. For recent methods of synthesis of cyclic sulfamidates, see: Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885-894. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936. Nicolaou, K. C.; Huang, X.; Snyder, S. A. ; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
2. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180. For recent methods of synthesis of cyclic sulfamidates, see: Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885-894. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936. Nicolaou, K. C.; Huang, X.; Snyder, S. A. ; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
3. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180. For recent methods of synthesis of cyclic sulfamidates, see: Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885-894. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936. Nicolaou, K. C.; Huang, X.; Snyder, S. A. ; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
4. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180. For recent methods of synthesis of cyclic sulfamidates, see: Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885-894. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936. Nicolaou, K. C.; Huang, X.; Snyder, S. A. ; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
5. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180. For recent methods of synthesis of cyclic sulfamidates, see: Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885-894. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936. Nicolaou, K. C.; Huang, X.; Snyder, S. A. ; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
6. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180. For recent methods of synthesis of cyclic sulfamidates, see: Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885-894. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936. Nicolaou, K. C.; Huang, X.; Snyder, S. A. ; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
7. Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051-7091. Lohray, B. B.; Bhushan, V. Adv. Heterocycl. Chem. 1997, 68, 89-180. For recent methods of synthesis of cyclic sulfamidates, see: Lowe, G.; Reed, M. A. Tetrahedron: Asymmetry 1990, 1, 885-894. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936. Nicolaou, K. C.; Huang, X.; Snyder, S. A. ; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483.
8. Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. D. Synlett 1997, 22-26. Eskici, M.; Gallagher, T. Synlett 2000, 1360-1362.
9. Littler, B. J.; Gallagher, T.; Boddy, I. K.; Riordan, P. D. Synlett 1997, 22-26. Eskici, M.; Gallagher, T. Synlett 2000, 1360-1362.
10. Step b (Scheme 1) can be achieved by direct thermal displacement of a secondary O-sulfate, or by hydrolysis and subsequent Mitsunobu reaction. Thermal cyclization did lead to some loss of stereochemical integrity (up to 10% ee), the extent of which depended on the substrate involved. The chemistry in Scheme 1 has also been applied to the synthesis of substituted pyrrolidines using enolate 1 and enantiomerically pure 1,2-cyclic sulfates.
11. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
12. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
13. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
14. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
15. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
16. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
17. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
18. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
19. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
20. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
21. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
22. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
23. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
24. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
25. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
26. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
27. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
28. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
29. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
30. For general nucleophilic displacements of 1,2- and 1,3-cyclic sulfamidates, see: (a) Meunier, N.; Veith, U.; Jäger, V. Chem. Commun. 1996, 331-332. (b) Pound, M. K.; Davies, D. L.; Pilkington, M.; Sousa, M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915-1918. Synthesis of fluoroamines: (c) Posakony, J. J.; Tewson, T. J. Synthesis 2002, 766-770. (d) Posakony, J. J. ; Tewson, T. J. Synthesis 2002, 859-864. (e) Ok, D.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 1999, 40, 3831-3834. (f) Lyle, T. A.; Magill, C. A.; Pitzenberger, S. M. J. Am. Chem. Soc. 1987, 109, 7890-7891. (g) Thompson, W. J.; Anderson, P. S.; Britcher, S. F.; Lyle, T. A.; Thies, J. E.; Magill, C. A.; Varga, S. L.; Schwering, J. E.; Lyle, P. A.; Christy, M. E.; Evans, B. E.; Colton, C. D.; Holloway, M. K.; Springer, J. P.; Hirshfield, J. M.; Ball, R. G.; Amato, J. S.; Larsen, R. D.; Wong, E. H. F.; Kemp, J. A.; Tricklebank, M. D.; Singh, L.; Oles, R.; Priestly, T.; Marshall, G. R.; Knight, A. R.; Middlemiss, D. N.; Woodruff, G. N.; Iversen, L. L. J. Med. Chem. 1990, 33, 789-808. (h) Van Dort, M. E.; Jung, Y.-W.; Sherman, P. S.; Kilbourn, M. R.; Wieland, D. M. J. Med. Chem. 1995, 38, 810-815. Synthesis of chiral ether ligands: (i) Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585-4586. In manipulating carbohydrates: (j) Aguilera, B.; Fernández-Mayoralas, A. Chem. Commun. 1996, 127-128. (k) Aguilera, B.; Fernández-Mayoralas, A.; Jaramillo, C. Tetrahedron 1997, 53, 5863-5876. (l) Aguilera, B.; Fernandez-Mayoralas, A. J. Org. Chem. 1998, 63, 2719-2723. Manipulation of α-amino acids, including serine derivatives: (m) Baldwin, J. E.; Spivey, A. C.; Schofield, C. J. Tetrahedron: Asymmetry 1990, 1, 881-884. (n) Boulton, L. T.; Stock, H. T.; Raphy, J.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1999, 1421-1429. (o) Wei, L.; Lubell, W. D. Org. Lett. 2000, 2, 2595-2598. (p) Wei, L.; Lubell, W. D. Can. J. Chem. 2001, 79, 94-104. (q) Atfani, M.; Wei, L.; Lubell, W. D. Org. Lett. 2001, 3, 2965-2968. (r) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407. (s) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543. Synthesis of 2-substituted pyrrolidines: (t) Cooper, G. F.; McCarthy, K. E.; Martin, M. G. Tetrahedron Lett. 1992, 33, 5895-5896.
31. Thiomorpholin-3-ones, including 5d, have also been prepared efficiently by reaction of oxazolinidin-2-ones with ethyl thioglycolate. Ishibashi, H.; Uegaki, M.; Sakai, M. Synlett 1997, 915-916. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
32. Thiomorpholin-3-ones, including 5d, have also been prepared efficiently by reaction of oxazolinidin-2-ones with ethyl thioglycolate. Ishibashi, H.; Uegaki, M.; Sakai, M. Synlett 1997, 915-916. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
33. 4q of the procedure reported by Garst (White, G. J.; Garst, M. E. J. Org. Chem. 1991, 56, 3177-3178).
34. 4h 3c, and 3d were prepared from the corresponding amino alcohols using essentially the same procedures as those used for 3a. In the case of 3c, racemic amino alcohol was used.
35. The cis and trans morpholine analogues of 5b are known (Spassov, S. L.; Stefanovsky, J. N.; Kurtev B. J.; Fodor, G. Chem. Ber. 1972, 105, 2467-2475), but the coupling constants associated with H(5) and H(6) that were reported did not correlate well to those observed for 5b. For this reason, the relative configuration of 5b was established by X-ray crystallographic analysis.
36. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
37. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
38. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
39. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
40. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
41. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
42. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
43. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
44. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
45. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
46. For the synthesis of C-substituted piperazines and piperazinones, see: Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063-3067. Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 4177-4183. Schanen, V.; Cherrier, M. P. ; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833-837. Nefzi, A.; Giulianotti, M. A.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 8539-8542. Dinsmore, C. J.; Zartman, C. B. Tetrahedron Lett. 2000, 41, 6309-6312. Rubsam, F.; Mazitschek, R.; Giannis, A. Tetrahedron 2000, 56, 8481-8487. González-Gómez, J. C.; Uriarte-Villares, E.; Figueroa-Pé rez, S. Synlett 2002, 1085-1088. Viso, A.; de la Pradilla, R. F.; López-Rodríguez, M. L.; García, A.; Tortosa, M. Synlett 2002, 755-758. Beshore, D. C.; Dinsmore, C. J. Org. Lett. 2002, 4, 1201-1204.
47. The stereochemistry of 7e is based on comparison with 5b, the structure of which was unambiguously assigned (see Figure 1).
48. Azide displacement: Li, G.; Chang, H. T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454. Amine nucleophiles require 125°C in a steel bomb: Zubovics, Z.; Toldy, L.; Varro, A.; Rabloczky, G.; Kurthy, M.; Dvortsak, P.; Jerkovich, G.; Tomori, E. Eur. J. Med. Chem. 1986, 21, 370-378.
49. Azide displacement: Li, G.; Chang, H. T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454. Amine nucleophiles require 125°C in a steel bomb: Zubovics, Z.; Toldy, L.; Varro, A.; Rabloczky, G.; Kurthy, M.; Dvortsak, P.; Jerkovich, G.; Tomori, E. Eur. J. Med. Chem. 1986, 21, 370-378.
50. Mori, K.; Tominaga, M.; Takigawa, T.; Matsui, M. Synthesis 1973, 790-791. Högberg, T.; Ström, P.; Ebner, M.; Rämsby, S. J. Org. Chem. 1987, 52, 2033-2036.
51. Mori, K.; Tominaga, M.; Takigawa, T.; Matsui, M. Synthesis 1973, 790-791. Högberg, T.; Ström, P.; Ebner, M.; Rämsby, S. J. Org. Chem. 1987, 52, 2033-2036.
52. In the case of 7f, NaCN in MeOH at reflux was more efficient than use of EtOH at 50°C. Formation of 7g via thermal lactamization (xylene, 5 days, reflux) proceeded in 48% yield, and no stereochemical scrambling at C(8a) was observed. Piperazine 7g was also isolated in 50% yield using NaCN (10 mol %) in MeOH at reflux. Cyanide may mediate lactamization via transesterification when MeOH is used as a solvent, but 7g was formed efficiently using EtOH as a solvent.
53. 4c but attempts to prevent production of 11 (a major byproduct under our standard conditions) using NaOH led to low mass recovery. Also, lactamization to give 10 occurred directly following neutralization.