Synthesis of polysubstituted pyrrolidines from cyclic sulfate esters and enamines

Synlett

Volumn , Issue 5, 2003, Pages 675-678

  O'Leary, Jane ^a   Colli, Corrado ^a   Wallis, John D ^a  

^a NOTTINGHAM TRENT UNIVERSITY   (United Kingdom)

Author keywords

Carbanions; Cyclic sulfates; Enamines; Heterocycles; Pyrrolidines

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ENAMINE; ESTER DERIVATIVE; METHYL GROUP; PYRROLIDINE DERIVATIVE; SULFATE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0037278650     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38350     Document Type: Article

References (23)

1. Lohray, B. B.; Bushan, V. V. Adv. Heterocycl. Chem. 1997, 68, 89.
2. (a) Wallis, J. D.; Karrer, A.; Dunitz, J. D. Helv. Chim. Acta 1986, 69, 69.
3. (b) Wallis, J. D.; Dunitz, J. D. Acta Crystallogr., Sect. C 1988, 44, 1037.
4. (a) Leurquin, F.; Ozturk, T.; Pilkington, M.; Wallis, J. D. J. Chem. Soc., Perkin Trans. 1 1997, 3173.
5. (b) Saygili, N.; Brown, R. B.; Day, P.; Hoelzl, R.; Kathirgamanathan, P.; Ozturk, T.; Pilkington, M.; Qayyum, M. M. B.; Turner, S. S.; Vorwerg, L.; Wallis, J. D. Tetrahedron 2001, 57, 5015.
6. Oi, R.; Sharpless, K. B. Tetrahedron Lett. 1991, 32, 999.
7. Lohray, B. B.; Gao, Y.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623.
8. Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241.
9. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
10. Burgess, K.; Li, W. Tetrahedron Lett. 1995, 36, 2725.
11. Hercouet, A.; Le Corre, M.; Carboni, B. Tetrahedron Lett. 2000, 41, 197.
12. Pound, M.; Davies, D. L.; Pilkington, M.; Pina Vaz Sousa, M. M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915.
13. 2), 2.04 (1 H, m
14. -1, T = 120 (2) K, 3879 unique reflections, 3027 with F>4σ(F), R = 0.058, wR = 0.141. Data deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ with reference CCDC 193354.
15. Bartoli, G.; Bosco, M.; Cimarelli, C.; Dalpozzo, R.; Palmieri, G. J. Chem. Soc., Perkin Trans. 1 1992, 2095.
16. 18NO requires 168.1388.
17. Lygo, B. Synlett 1993, 734.
18. Sosnicki, J. G.; Liebscher, J. Synlett 1996, 1117.
19. (a) Hodgkinson, T. J.; Kelland, L. R.; Shipman, M.; Vile, J. Tetrahedron 1998, 6029.
20. (b) Mulzer, J.; List, B.; Bats, J. W. J. Am. Chem. Soc. 1997, 119, 5512.
21. Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833.
22. Khoukhi, N.; Vaultier, M.; Carrie, R. Tetrahedron 1987, 43, 1811.
23. Eskici, M.; Gallagher, T. Synlett 2000, 1360.