Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes

Synthetic applications of cyclobutanones other than ring expansion and fragmentation reactions are rare. Herein, highly efficient diastereo‐ and enantioselective organocatalytic Michael additions of 2‐substituted cyclobutanone derivatives to nitroalkenes are reported allowing the stereocontrolled cr...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2012-12, Vol.354 (18), p.3523-3532
Main Authors: Mailhol, Damien, Duque, Maria del Mar Sanchez, Raimondi, Wilfried, Bonne, Damien, Constantieux, Thierry, Coquerel, Yoann, Rodriguez, Jean
Format: Article
Language:English
Subjects:
Activation
Amides
asymmetric catalysis
Catalysis
Chemical Sciences
CC bond formation
Derivatives
Fragmentation
Michael addition
Michael reaction
organic catalysis
Organic chemistry
Stabilization
strained molecules
Synthesis
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Summary:Synthetic applications of cyclobutanones other than ring expansion and fragmentation reactions are rare. Herein, highly efficient diastereo‐ and enantioselective organocatalytic Michael additions of 2‐substituted cyclobutanone derivatives to nitroalkenes are reported allowing the stereocontrolled creation of ‘all‐carbon’ quaternary centers. The approach relies on both the use of Brønsted base/hydrogen‐bond donor bifunctional organocatalysts, and importantly, the specific stabilization and activation of cyclobutanone with a secondary amide moiety. The reaction was found to nicely accommodate a broad scope of substrates, allowing the control of up to three contiguous stereogenic centers. This work has opened new synthetic opportunities.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201200658