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Highly Enantioselective Addition of Trimethylsilylacetylene to Aldehydes Catalyzed by a Zinc–Amino‐Alcohol Complex
Author(s) -
Li ZhiYuan,
Wang Min,
Bian QingHua,
Zheng Bing,
Mao JianYou,
Li ShuoNing,
Liu ShangZhong,
Wang MingAn,
Zhong JiangChun,
Guo HongChao
Publication year - 2011
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.201100535
Subject(s) - enantioselective synthesis , alcohol , chemistry , zinc , catalysis , organic chemistry , trimethylsilyl , aryl , alkyl , combinatorial chemistry
A fine addition! A highly enantioselective and efficient procedure for the amino‐alcohol–zinc‐catalyzed addition of trimethylsilylacetylene to aromatic, α,β‐unsaturated, and aliphatic aldehydes has been developed (see scheme; R=aryl, alkynyl, or alkyl; TMS=trimethylsilyl; TBDMS= tert ‐butyldimethylsilyl). The present protocol was successfully applied in the concise synthesis of the natural products marine alkynol and falcarindiol.