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Catalytic Asymmetric Synthesis of γ‐Substituted Vinyl Sulfones
Author(s) -
López Rosa,
Zalacain Maitane,
Palomo Claudio
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003177
Subject(s) - sulfonyl , catalysis , amine gas treating , conjugate , chemistry , stereoselectivity , base (topology) , combinatorial chemistry , organic base , organic chemistry , organic synthesis , mathematics , mathematical analysis , alkyl
A fast new entry for the stereoselective construction of γ‐substituted vinyl sulfones is presented. The key for success is the use of a readily available chiral secondary amine catalyst that allows the use of base‐sensitive β‐nitroethyl sulfones as masked β‐sulfonyl vinyl anions in conjugate additions. The method performed in a three‐step one‐pot operation gives access to a great variety of vinyl sulfones in good yields and with excellent enantioselectivities. The method has also been extended to other relatively base‐sensitive β‐electron‐withdrawing‐substituted nitroalkanes to afford products with manifold functionality, providing a quick entry to very attractive synthetic intermediates for organic synthesis.