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Direct Catalytic Asymmetric Addition of Allylic Cyanides to Aldehydes for Expeditious Access to Enantioenriched Unsaturated δ‐Valerolactones
Author(s) -
Otsuka Yasunari,
Takada Hisashi,
Yasuda Shigeo,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201201021
Subject(s) - nitrile , catalysis , lewis acids and bases , allylic rearrangement , cyanide , chemistry , brønsted–lowry acid–base theory , base (topology) , organic chemistry , enantioselective synthesis , combinatorial chemistry , mathematics , mathematical analysis
A direct catalytic asymmetric γ‐addition of allyl cyanide to aldehydes promoted by soft Lewis acid/hard Brønsted base cooperative catalysis is described. The resulting homoallylic alcohols bearing a Z ‐configured α,β‐unsaturated nitrile allow rapid access to enantioenriched δ‐valerolactones.