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Lewis Base Catalyzed Enantioselective Allylation of α,β‐Unsaturated Aldehydes
Author(s) -
Kadlčíková Aneta,
Valterová Irena,
Ducháčková Lucie,
Roithová Jana,
Kotora Martin
Publication year - 2010
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.201001523
Subject(s) - enantioselective synthesis , catalysis , chemistry , lewis acids and bases , base (topology) , tetrahydroisoquinoline , aldehyde , organic chemistry , mathematical analysis , mathematics
Being selective : The catalytic allylation of α,β‐unsaturated aldehydes with allyltrichlorosilane in the presence of chiral 3,3′‐unsymmetrically substituted bis(tetrahydroisoquinoline) N , N ‐dioxides was explored. The allylation of various aldehydes proceeded under mild reaction conditions (−78 °C) with high yields and enantioselectivity (see scheme). This allylation was applied in the synthesis of ( S )‐(−)‐goniothalamin.
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