Enantioselective Mannich-Type Reaction Catalyzed by a Chiral Brønsted Acid

No metal required: The Mannich‐type reaction of ketene silyl acetals 2 with aldimines 1 proceeded highly enantioselectively to afford the syn isomer of β‐aminoesters 3 with up to 96 % ee under the influence of a chiral Brønsted acid 4 derived from (R)‐BINOL.

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-03, Vol.43 (12), p.1566-1568
Main Authors: Akiyama, Takahiko, Itoh, Junji, Yokota, Koji, Fuchibe, Kohei
Format: Article
Language:English
Subjects:
Acids - chemistry
asymmetric synthesis
Brønsted acids
Catalysis
enantioselectivity
Ethylenes - chemical synthesis
Ethylenes - chemistry
Imines - chemical synthesis
Imines - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Conformation
Molecular Structure
organocatalysis
Schiff bases
Stereoisomerism
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Description
Summary:No metal required: The Mannich‐type reaction of ketene silyl acetals 2 with aldimines 1 proceeded highly enantioselectively to afford the syn isomer of β‐aminoesters 3 with up to 96 % ee under the influence of a chiral Brønsted acid 4 derived from (R)‐BINOL.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353240