A rapid assembly of homochiral 2,3,4-trisubstituted pyrrolidines

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1647-1650

  Jones, Raymond C F ^a   Howard, Kevin J ^a   Snaith, John S ^a  

^a OPEN UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031550851     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00111-1     Document Type: Article

References (16)

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2. 2. For a recent review see: Parsons, A.F. Tetrahedron, 1996, 52, 4149-4174.
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7. (e) Monn, J.A.; Valli, M. J. J. Org. Chem., 1994, 59, 2773-2778.
8. 4. (a) Jones, R. C. F.; Howard, K.J.; Snaith, J.S. Tetrahedron Lett., 1996, 37, 1707-1710;
9. (b) Jones, R. C. F.; Howard, K.J.; Snaith, J.S. Tetrahedron Lett., 1996, 37, 1711-1714.
10. 5 All new compounds gave spectral data (IR, UV, NMR, MS) in accord with the assigned structure, and satisfactory combustion analysis or accurate mass measurement.
11. 6 Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc., 1980, 102, 4743-4763.
12. 7. Baldwin, J. E.; Mackenzie Turner, S. C.; Moloney, M. G. Synlett, 1994, 925-928.
13. +, 28%), 374 (37), 245 (30), 235 (59), 120 (44), 104 (71), 91 (100) and 77 (60).
14. 9. We thank Dr A.J. Blake, University of Nottingham, for this determination.
15. -1 more exothermic than that for the C-6 epimer that would be predicted from our transition state model with Z-dipolarophile 8. This stability difference, if reflected in the transition states, may explain the reluctance of 8 to undergo the cycloaddition before alternative degradation intervenes.
16. +, 7%). Cf. Bellamy, L. J. The Infrared Spectra of Complex Molecules, 2nd ed.; Methuen: London, 1958; p. 213.