Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis ofproline and pipecolic acid derivatives

Authors
Davis, FA Zhang, HM Lee, SH
Citation
Fa. Davis et al., Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis ofproline and pipecolic acid derivatives, ORG LETT, 3(5), 2001, pp. 759-762
Citations number
47
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
5
Year of publication
2001
Pages
759 - 762
Database
ISI
SICI code
1523-7060(20010308)3:5<759:MOS(II>2.0.ZU;2-B
Abstract
[GRAPHICS] On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha -amino ni triles that afford oxo alpha -amino acids on hydrolysis. These amino acids cyclize and are reduced to cis proline and cis pipecolic acids derivatives in high ee and good yield. This new procedure avoids many of the limitation s related to the preparation of oxo amino acids from proteinogenic amino ac ids.