Cooperative Dienamine/Hydrogen-Bonding Catalysis: Enantioselective Formal [2+2] Cycloaddition of Enals with Nitroalkenes

Two can play this game: The title reaction is catalyzed by a chiral secondary amine in the presence of an achiral thiourea for the enantio‐ and diastereoselective synthesis of highly functionalized cyclobutanes (see scheme; TMS=trimethylsilyl). Mechanistically, two consecutive Michael reactions proc...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-04, Vol.51 (17), p.4104-4107
Main Authors: Talavera, Garazi, Reyes, Efraím, Vicario, Jose L., Carrillo, Luisa
Format: Article
Language:English
Subjects:
Activation
Alkenes - chemistry
Amines
asymmetric synthesis
carbocycles
Catalysis
Cycloaddition
cycloadditions
Cyclobutane
Cyclobutanes - chemical synthesis
Games
Hydrogen Bonding
Methods
Michael addition
Michael reaction
Nitro Compounds - chemistry
Organic Chemistry Phenomena
organocatalysis
Synthesis
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Summary:Two can play this game: The title reaction is catalyzed by a chiral secondary amine in the presence of an achiral thiourea for the enantio‐ and diastereoselective synthesis of highly functionalized cyclobutanes (see scheme; TMS=trimethylsilyl). Mechanistically, two consecutive Michael reactions proceed through an unprecedented combination of an dienamine/iminium activation mode.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201200269