A New Strategy for the Diastereoselective Synthesis of Polyfunctionalized Pyrrolidines

Synlett

Volumn , Issue 1, 2004, Pages 49-52

  Davis, Andrew S ^a   Gates, Nicole J ^a   Lindsay, Karl B ^a   Tang, Minyan ^a   Pyne, Stephen G ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

Dihydroxylation; Oxazolindones; Pyrrolidines; Ring closing metathesis

Indexed keywords

KETONE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CIS ISOMER; DIASTEREOISOMER; DIHYDROXYLATION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0347601837     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43362     Document Type: Article

References (35)

1. Lindsay, K. B.; Tang, M.; Pyne, S. G. Synlett 2002, 731.
2. Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774.
3. (3) For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
4. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
5. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
6. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
7. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
8. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
9. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
10. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
11. For the application of the ring-closing metathesis reaction to the synthesis of aza-sugars see: (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621. (b) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547. (c) Huwe, C. M.; Blechert, S. Synthesis 1997, 61. (d) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359. (e) Lindstrom, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173. (f) Ovaa, H.; Stragies, R. ; van der Marcel, G. A.; van Boom, J. H.; Blechert, S. Chem. Commun. 2000, 1501. (g) Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079. (h) Klitze, C. F.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 5605. (i) Chandra, K. L.; Chandrasekhar, M.; Singh, V. K. J. Org. Chem. 2002, 67, 4630.
12. (4) For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
13. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
14. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
15. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
16. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
17. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
18. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
19. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
20. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. (i) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
21. For the application of the ring-closing metathesis reaction to the synthesis of 2,5-dihydropyrroles from dienes see: (a) Huwe, C. M.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 2376. (b) Fürstner, A. ; Picquet, M.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1998, 1315. (c) Cerezo, S.; Cortes, J.; Moreno-Manas, M.; Pleixats, R.; Roglans, A. Tetrahedron 1998, 54, 14869. (d) Fürstner, A.; Ackermann, L. Chem. Commun. 1999, 95. (e) Bujard, M.; Briot, A.; Gouverneur, V.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 8795. (f) Fürstner, A.; Liebl, M.; Hill, A. F.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601. (g) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Hermann, W. A. Tetrahedron Lett. 1999, 40, 4787. (h) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657. Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929. (j) Hunt, J. C. A.; Laurent, P.; Moody, C. J. Chem. Commun. 2000, 1771.
22. (a) Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 67.
23. (b) Agami, C.; Couty, F.; Rabasso, N. Tetrahedron Lett. 2000, 41, 4113.
24. (c) Martín, R.; Moyano, A.; Pericàs, M. A.; Riera, A. Org. Lett. 2000, 2, 93.
25. (d) Agami, C.; Couty, F.; Rabasso, N. Tetrahedron 2001, 57, 5393.
26. (e) Fustero, S.; Navarro, A.; Pina, B.; Soler Juan, G.; Bartolome, A.; Asensio, A.; Simon, A.; Bravo, P.; Fronza, G.; Volonterio, A.; Zanda, M. Org. Lett. 2001, 3, 2621.
27. For the RCM of 4-allyl-5-allyl-2-oxazilidinones and its 5-homo analogue see: Agami, C.; Couty, F.; Rabasso, N. Tetrahedron Lett. 2001, 42, 4633.
28. 3): 5 = 54.6 (t, C5), 64.5 (d, C7a), 68.6 (t, C4), 128.9, 130.6 (d, C6 and C7), 163.2 (s, C2).
29. 3): 5 = 21.3 (t, C8), 29.2, 34.9 (t, Cl, C9), 54.4 (t, C5), 55.1 (q, C16), 69.3 (t, C10), 70.3 (d, C2), 72.4 (t, C11), 81.8 (d, C6), 113.6 (d, C14), 128.5 (d, C3), 129.1 (d, C13), 1 30.4 (s, C12), 130.5 (d, C4), 159.0 (s, C15), 162.5 (s, C17).
30. 1.2 followed by oxazolidinone formation as described above or by using triphosgene/ triethylamine.
31. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
32. 12
33. Huang, Y.; Dalton, D. R. J. Org. Chem. 1997, 62, 372.
34. de Vicente, J.; Arrayas, R. G.; Canada, J.; Carretero, J. C. Sylett 2000, 53.
35. Mukai, C.; Sugimoto, Y.-i.; Miyazawa, K.; Yamaguchi, S.; Hanaoka, M. J. Org. Chem. 1998, 63, 6281.