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Catalytic Enantioselective Synthesis of α‐Substituted Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via Vinylaluminum Reagents
Author(s) -
Kumar Ravindra,
Kawasaki Hiroki,
Harada Toshiro
Publication year - 2013
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.201303619
Subject(s) - enantioselective synthesis , allylic rearrangement , reagent , aldehyde , catalysis , chemistry , organic chemistry , combinatorial chemistry
One‐pot procedure : A general method for the highly enantioselective synthesis of α‐substituted allylic alcohols has been developed starting from readily available terminal alkynes and aldehydes and proceeding via vinylaluminum reagents (see scheme, dppp=1,3‐bis(diphenylphosphino)propane). The use of Me 2 AlH is essential in the Ni‐catalyzed hydroalumination step to generate vinylaluminum reagents that cannot reduce the aldehyde.