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A Straightforward Organocatalytic Alkylation of 2‐Arylacetaldehydes: An Approach towards Bisabolanes
Author(s) -
Gualandi Andrea,
Canestrari Pietro,
Emer Enrico,
Cozzi Pier Giorgio
Publication year - 2014
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.201300250
Subject(s) - alkylation , chemistry , stereoselectivity , tetrafluoroborate , enantioselective synthesis , acetonitrile , catalysis , organocatalysis , organic chemistry , combinatorial chemistry , ionic liquid
A highly stereoselective organocatalytic α‐alkylation of 2‐arylacetaldehydes with a commercially available carbenium tetrafluoroborate is described. The stereoselective alkylation was carried out in acetonitrile/water, under air in the presence of a commercially available imidazolidinone (MacMillan’s catalyst). Key intermediates for the synthesis of bisabolanes were obtained through a simple chemistry. In particular a direct, enantioselective and facile synthesis of ( R )‐(−)‐curcumene is described.
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