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Chiral borated esters in asymmetric synthesis: 1. the first asymmetric reaction catalyzed by chiral spiroborated esters with an O 3 BN framework
Author(s) -
Liu DeJun,
Shan ZiXing,
Qin JinGui
Publication year - 2004
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20040221124
Subject(s) - chemistry , acetophenone , stereoselectivity , catalysis , yield (engineering) , enantioselective synthesis , medicinal chemistry , reaction conditions , stereochemistry , organic chemistry , materials science , metallurgy
The first asymmetric reaction catalyzed by chiral spiroborated esters with an O 3 BN framework was reported. In the presence of 0.1 equivalent of ( R,S )‐1 or ( S,S )‐1, acetophenone was reduced by 0.6 equivalent of borne in THF at 0–5 °C for 2 h to give (R)‐1‐phenylethanol of up to 76% ee and 73% isolated yield. Influence of reaction conditions on the stereoselectivity of the reduction was investigated and a possible catalytic mechanism of the chiral spiroborated esters toward the reduction was also suggested.