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Chiral N-Heterocyclic Carbene Catalyzed Staudinger Reaction of Ketenes with Imines: Highly Enantioselective Synthesis of N-Boc -Lactams.
- Source :
-
Organic Letters . Jan2008, Vol. 10 Issue 2, p277-280. 4p. - Publication Year :
- 2008
-
Abstract
- N-Heterocyclic carbenes (NHCs) were demonstrated to be efficient catalysts for the Staudinger reaction of ketenes with N-tosyl, N-benzyloxycarbonyl, or N-tert-butoxycarbonyl imines. Chiral NHC 8b, conveniently prepared from l-pyroglutamic acid, catalyzed the reactions of arylalkylketenes with a variety of N-tert-butoxycarbonyl arylimines to give the corresponding cis--lactams in good yields with good diastereoselectivities and excellent enantioselectivities (up to 99% ee). Two possible catalytic pathways, initiated by the addition of NHC to ketenes or imines, were discussed. [ABSTRACT FROM AUTHOR]
- Subjects :
- *OXO compounds
*ORGANONITROGEN compounds
*HETEROCYCLIC compounds
*KETENES
Subjects
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 10
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Organic Letters
- Publication Type :
- Academic Journal
- Accession number :
- 28693669
- Full Text :
- https://doi.org/10.1021/ol702759b