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Enantioselective Allylation of tert ‐Butyldimethylsilyl‐Protected Vanillin and Synthesis of a Lignan Derivative Isolated from Machilus wangchiana
Author(s) -
Cadart Timothée,
Koukal Petr,
Kotora Martin
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403094
Subject(s) - enantioselective synthesis , chemistry , lignan , vanillin , diastereomer , derivative (finance) , organic chemistry , stereochemistry , catalysis , financial economics , economics
Various enantioselective allylations and crotylations of tert ‐butyldimethylsilyl‐protected vanillin were undertaken to assess the best methodology to provide the corresponding homoallylic alcohols in high yields with high enantiopurity. In general, most of the tested allylations proceeded with high enantioselectivities (>92 % ee ) and in the case of crotylation also with excellent diastereoselectivity (96 % ee , >98 % de ). The product obtained from the crotylation reaction was used in the enantioselective synthesis of the unnatural diastereoisomer of a recently isolated lignan derivative.