Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors

Authors
Betancort, JM Barbas, CF
Citation
Jm. Betancort et Cf. Barbas, Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors, ORG LETT, 3(23), 2001, pp. 3737-3740
Citations number
50
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
23
Year of publication
2001
Pages
3737 - 3740
Database
ISI
SICI code
1523-7060(20011115)3:23<3737:CDAMRT>2.0.ZU;2-P
Abstract
[GRAPHICS] Direct catalytic enantio- and diastereoselective Michael addition reactions of unmodified aldehydes to nitro olefins using (S)-2-(morpholinomethyl)-py rrolidine as a catalyst are described. The reactions proceed in good yield (up to 96%) in a highly syn-selective manner (up to 98:2) with enantloselec tivities approaching 80%. The resulting gamma -formyl nitro compounds are r eadily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.