Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis

Journal of the American Chemical Society

Volumn 125, Issue 34, 2003, Pages 10174-10175

  Chen, Chuo ^a   Li, Xiaodong ^a   Schreiber, Stuart L ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDE;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRALITY; DERIVATIZATION; ENANTIOMER; LIGAND BINDING; REACTION ANALYSIS; STEREOSPECIFICITY;

ALDEHYDES; AZO COMPOUNDS; CATALYSIS; CYCLIZATION; ESTERS; IMINO ACIDS;

EID: 0041931082     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036558z     Document Type: Article

References (30)

1. For reviews, see: (a) Kanemasa, S. Synlett 2002, 1371-1387.
2. (b) Grigg, R. Chem. Soc. Rev. 1987, 16, 89-121.
3. (c) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Padwa, A., Pearson, W., Eds; Wiley-VCH: Weinheim, 2002; pp 169-252.
4. Schreiber, S. L. Science 2000, 287, 1964-1969.
5. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
6. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
7. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
8. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
9. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
10. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
11. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
12. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
13. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
14. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
15. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
16. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
17. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
18. Only azomethine ylides derived from aldehydes and α-aminoesters are reviewed here. (a) Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T. Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857-2865. (b) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481. (c) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.; Pilati, T. Tetrahedron: Asymmetry 1991, 2, 1329-1342. (d) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431-10442. (e) Waldmann, H.; Blaeser, E.; Jansen, M.; Letschert, H.-P. Chem.-Eur. J. 1995, 1, 150-154. (f) Pyne, S. G.; Safaei-G., J.; Koller, F. Tetrahedron Lett. 1995, 36, 2511-2514. (g) Barr, D. A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 1995, 51, 273-294. (h) Cooper, D. M.; Grigg, R.; Hargreaves, S.; Kennewell, P.; Redpath, J. Tetrahedron 1995, 51, 7791-7808. (i) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (j) Schnell, B.; Bernardinelli, G.; Kündig, E. P. Synlett 1999, 348-350. (k) Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170-1179. (l) Garner, P.; Dogan, O.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71-85. (m) Dogan, Ö.; Öner, I.; Ülkü, D.; Arici, C. Tetrahedron: Asymmetry 2002, 13, 2099-2104. (n) See also ref 6b.
19. Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 13400-13401.
20. Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 4236-4238.
21. For the early development of catalytic asymmetric [3+2] azomethine ylidecycloaddition, see: (a) Allway, P.; Grigg, R. Tetrahedron Lett. 1991, 32, 5817-5820.
22. For the early development of catalytic asymmetric [3+2] azomethine ylidecycloaddition, see: (a) Allway, P.; Grigg, R. Tetrahedron Lett. 1991, 32, 5817-5820.
23. While the silver system gives better selectivity and has a broader scope than the zinc(II) system, the xylyl-FAP ligand requires an eight-step synthesis. The zinc(II) system resulted in low conversions on the solid phase (500 μm polystyrene beads). The (R,R)-t-BuBOX is not commercially available.
24. (a) Blackwell, H. E.; Pérez, L.; Stavenger, R. A.; Tallarico, J. A.; Cope Eatough, E.; Foley, M. A.; Schreiber, S. L. Chem. Biol. 2001, 8, 1167-1182. (b) Clemons, P. A.; Koehler, A. N.; Wagner, B. K.; Sprigings, T. G.; Spring, D. R.; King, R. W.; Schreiber, S. L.; Foley, M. A. Chem. Biol. 2001, 8, 1183-1195.
25. (a) Blackwell, H. E.; Pérez, L.; Stavenger, R. A.; Tallarico, J. A.; Cope Eatough, E.; Foley, M. A.; Schreiber, S. L. Chem. Biol. 2001, 8, 1167-1182. (b) Clemons, P. A.; Koehler, A. N.; Wagner, B. K.; Sprigings, T. G.; Spring, D. R.; King, R. W.; Schreiber, S. L.; Foley, M. A. Chem. Biol. 2001, 8, 1183-1195.
26. In this case, the QUINAP ligand (4) showed superior reactivity as it took 48 h at 0°C for 3 mol% of silver acetate/xylyl-FAP to complete the reaction. For details, see Supporting Information.
27. The silver/xylyl-FAP catalyst system was reported to give 87% yield and 87% ee after reacting at 0°C for 7 h (ref 4).
28. It was reported that condensing aldehydes with α-amino acids or esters provided racemic iminoacids or iminoesters. Grigg, R.; Gunaratne, H. Q. N. Tetrahedron Lett. 1983, 24, 4457-4460.
29. Only three scattered examples of catalytic asymmetric [3+2] azomethine cycloaddition reactions using iminoesters derived from amino acid other than glycine were reported. (a) Reference 6b: Iminoester generated from naphthaldehyde and alanine, reacting with methyl vinyl ketone (83% yield, 70% ee) or phenyl vinyl sulfone (64% yield, 70% ee). (b) Longimire, J. M. Ph. D. Dissertation, Penn State University, 2000; iminoester 26 reacting with dimethyl maleate: 70% yield. 65% ee.
30. Only three scattered examples of catalytic asymmetric [3+2] azomethine cycloaddition reactions using iminoesters derived from amino acid other than glycine were reported. (a) Reference 6b: Iminoester generated from naphthaldehyde and alanine, reacting with methyl vinyl ketone (83% yield, 70% ee) or phenyl vinyl sulfone (64% yield, 70% ee). (b) Longimire, J. M. Ph. D. Dissertation, Penn State University, 2000; iminoester 26 reacting with dimethyl maleate: 70% yield. 65% ee.