Premium
Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes
Author(s) -
Mailhol Damien,
Duque Maria del Mar Sanchez,
Raimondi Wilfried,
Bonne Damien,
Constantieux Thierry,
Coquerel Yoann,
Rodriguez Jean
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200658
Subject(s) - chemistry , enantioselective synthesis , stereocenter , organocatalysis , michael reaction , bifunctional , cyclobutanone , moiety , combinatorial chemistry , stereochemistry , organic chemistry , ring (chemistry) , catalysis
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.