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Enzyme‐ and Ruthenium‐Catalyzed Enantioselective Transformation of α‐Allenic Alcohols into 2,3‐Dihydrofurans
Author(s) -
Yang Bin,
Zhu Can,
Qiu Youai,
Bäckvall JanE.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601505
Subject(s) - cycloisomerization , ruthenium , enantioselective synthesis , chemistry , kinetic resolution , carbene , catalysis , transformation (genetics) , combinatorial chemistry , enzyme , organic chemistry , stereochemistry , biochemistry , gene
An efficient one‐pot method for the enzyme‐ and ruthenium‐catalyzed enantioselective transformation of α‐allenic alcohols into 2,3‐dihydrofurans has been developed. The method involves an enzymatic kinetic resolution and a subsequent ruthenium‐catalyzed cycloisomerization, which provides 2,3‐dihydrofurans with excellent enantioselectivity (up to >99 % ee ). A ruthenium carbene species was proposed as a key intermediate in the cycloisomerization.