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Enantioselective Synthesis of β‐Pyrazole‐Substituted Alcohols through an Asymmetric Ring‐Opening Reaction of meso ‐Epoxides
Author(s) -
Hu Xiaolei,
Gao Bo,
Chu Yangyang,
Li Wei,
Liu Xiaohua,
Lin Lili,
Feng Xiaoming
Publication year - 2012
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.201103792
Subject(s) - pyrazole , enantioselective synthesis , ring (chemistry) , chemistry , nucleophile , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry
An efficient and practical synthesis of optically pure β‐pyrazole‐substituted alcohols was achieved by an asymmetric ring‐opening reaction of meso ‐epoxides with pyrazole derivatives as the nucleophile. In the presence of 1 mol % of an N,N′ ‐dioxide–Sc(OTf) 3 complex, excellent enantioselectivity and yields were obtained from meso ‐epoxides. The process could also be used for a mixture of cis ‐ and trans ‐stilbene oxides. A proposed transition‐state model is provided.