A Highly Efficient and Practical Method for Catalytic Asymmetric Vinylogous Mannich (AVM) Reactions

Very selective but very easy: These are two of the attributes of the asymmetric vinylogous Mannich reactions presented herein. These reactions can be run on a gram scale and in undistilled THF and air (see scheme; TMS=SiMe3). All that is needed is commercially available AgOAc, a readily available am...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2006-11, Vol.45 (43), p.7230-7233
Main Authors: Carswell, Emma L., Snapper, Marc L., Hoveyda, Amir H.
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
asymmetric catalysis
Catalysis
enantioselective synthesis
imines
Imines - chemistry
Molecular Structure
Organosilicon Compounds - chemistry
silver
Silver - chemistry
Stereoisomerism
vinylogous Mannich reactions
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Summary:Very selective but very easy: These are two of the attributes of the asymmetric vinylogous Mannich reactions presented herein. These reactions can be run on a gram scale and in undistilled THF and air (see scheme; TMS=SiMe3). All that is needed is commercially available AgOAc, a readily available amino acid derived phosphine, and a commercially available or easily prepared (one step) siloxyfuran.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200603496