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Enantioselective Friedel–Crafts Alkylation of Thiophenes with Ethyl Glyoxylate: Easy Access to Chiral Secondary Alcohols
Author(s) -
Huang Zhong,
Zhang Jingchang,
Zhou Yuqiang,
Wang NaiXing
Publication year - 2011
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.201001455
Subject(s) - chemistry , friedel–crafts reaction , enantioselective synthesis , alkylation , glyoxylate cycle , organic chemistry , catalysis , enzyme
Abstract Friedel–Crafts alkylation reactions of ethyl glyoxylate with various thiophenes to give the corresponding chiral secondary alcohols were demonstrated. The majority of these reactions proceeded with good enantioselectivities (up to 91 %) and satisfactory isolated yields. Notably, we found that 2‐substituted thiophenes underwent the reaction more smoothly than unsubstituted and 3‐substituted thiophenes.