The Scope of the Direct Proline-Catalyzed Asymmetric Addition of Ketones to Imines

A full account of catalytic direct asymmetric Mannich‐type reactions is presented describing the scope of amino acid‐catalyzed additions of unmodified ketones to a large variety of imines. These reactions are performed under very mild, operationally simple, and environmentally friendly and benign co...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2004-08, Vol.346 (9-10), p.1131-1140
Main Authors: Notz, Wolfgang, Watanabe, Shin-ichi, Chowdari, Naidu S., Zhong, Guofu, Betancort, Juan M., Tanaka, Fujie, Barbas III, Carlos F.
Format: Article
Language:English
Subjects:
asymmetric catalysis
CC bond formation
imines
ionic liquids
Mannich-type reactions
organic catalysis
γ-oxo-α-amino acids
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Summary:A full account of catalytic direct asymmetric Mannich‐type reactions is presented describing the scope of amino acid‐catalyzed additions of unmodified ketones to a large variety of imines. These reactions are performed under very mild, operationally simple, and environmentally friendly and benign conditions employing a one‐pot, three‐component protocol as well as preformed imines. Typically, products were obtained with high regio‐ and diastereoselectivities and excellent enantioselectivities. The methodology developed was applied as a powerful approach toward the synthesis of enantiomerically pure functionalized α‐amino acids, γ‐lactones, oxime‐functionalized amino acids as well as pharmacologically important targets such as (R)‐cyclohexylglycine.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200404114