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Nitroolefins as a Nucleophilic Component for Highly Stereoselective Aza Henry Reaction under the Catalysis of Chiral Ammonium Betaines
Author(s) -
Uraguchi Daisuke,
Oyaizu Keigo,
Ooi Takashi
Publication year - 2012
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.201201259
Subject(s) - stereoselectivity , nucleophile , catalysis , component (thermodynamics) , ammonium , chemistry , medicinal chemistry , organic chemistry , combinatorial chemistry , physics , thermodynamics
Vinylogous nitronate was successfully generated from β,β‐disubstituted nitroolefins for achieving a highly regio‐, diastereo‐, and enantioselective aza Henry reaction under the influence of chiral ammonium betaine of type 1 as an organic‐base catalyst. The present approach greatly expands the synthetic utility of nitroolefins in the development of carbon–carbon bond‐forming reactions (see scheme).