An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1711-1714

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

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b OPEN UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030005646     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00114-1     Document Type: Article

References (11)

1. Jones, R.C.F.; Howard, K.J.; Snaith, J.S. preceding Letter.
2. Jones, R.C.F.; Nichols, J.R.; Cox, M.T. Tetrahedron Lett., 1990, 31, 2333.
3. Jones, R.C.F.; Howard, K.J. J. Chem. Soc., Perkin Trans. 1, 1993, 2391.
4. 3CN was found to promote epimerisation, possibly due to the basic nature of the cyanoborohydride anion.
5. Olofson, R.A.; Martz, J.T.; Senet, J.-P.; Piteau, M.; Malfoot, T. J. Org. Chem, 1984, 49, 2081; Olofson, R.A.; Abbott, D.E. Ibid., 2795.
6. Olofson, R.A.; Martz, J.T.; Senet, J.-P.; Piteau, M.; Malfoot, T. J. Org. Chem, 1984, 49, 2081; Olofson, R.A.; Abbott, D.E. Ibid., 2795.
7. Jones, R.C.F; Howard, K.J.; Snaith, J.S.; Steel, P.J. manuscript in preparation.
8. Bridges, R.J.; Stanley, M.S.; Anderson, M.W.; Cotman, C.W.; Chamberlin, A.R. J. Med. Chem, 1991, 34, 717.
9. 2O and TFA) 33.69 (C-3), 44.26 (C-4), 50.22 (C-5), 62.19 (C-2), 173.47 and 177.64 (2 × CO).
10. 2O) for the enantiomer; Untch, K.G.; Gibbon, G.A. Tetrahedron Lett., 1964, 44, 3259}
11. 2O) for the enantiomer; Untch, K.G.; Gibbon, G.A. Tetrahedron Lett., 1964, 44, 3259}