Enantioselective Synthesis of α-Alkylidene-γ-Butyrolactones: Intramolecular Rauhut-Currier Reaction Promoted by Acid/Base Organocatalysts

Teaming up: The title reaction has been developed to deliver the product α‐alkylidene‐γ‐butyrolactones as single diastereomers with up to 98 % ee (see scheme; Ts=4‐toluenesulfonyl). The enantioselective process is catalyzed by 1, which contains both Lewis base and Brønsted acid moieties....

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-05, Vol.51 (22), p.5423-5426
Main Authors: Takizawa, Shinobu, Nguyen, Tue Minh-Nhat, Grossmann, André, Enders, Dieter, Sasai, Hiroaki
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
Acids - chemistry
Alkalies - chemistry
asymmetric catalysis
Catalysis
Cyclization
lactones
Michael addition
Molecular Structure
organocatalysis
Stereoisomerism
synthetic methods
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Summary:Teaming up: The title reaction has been developed to deliver the product α‐alkylidene‐γ‐butyrolactones as single diastereomers with up to 98 % ee (see scheme; Ts=4‐toluenesulfonyl). The enantioselective process is catalyzed by 1, which contains both Lewis base and Brønsted acid moieties.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201201542