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Tungsten‐Catalyzed Regio‐ and Enantioselective Aminolysis of trans ‐2,3‐Epoxy Alcohols: An Entry to Virtually Enantiopure Amino Alcohols
Author(s) -
Wang Chuan,
Yamamoto Hisashi
Publication year - 2014
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.201408732
Subject(s) - enantiopure drug , aminolysis , enantioselective synthesis , catalysis , chemistry , epoxy , stereospecificity , organic chemistry , combinatorial chemistry
The first catalytic enantioselective aminolysis of trans ‐2,3‐epoxy alcohols has been accomplished. This stereospecific ring‐opening process was efficiently promoted by a tungsten/bis(hydroxamic acid) catalytic system, furnishing various anti ‐3‐amino‐1,2‐diols with excellent regiocontrol and high enantioselectivities (up to 95 % ee ). Moreover, virtually enantiopure 3‐amino‐1,2‐diols could be obtained by the sequential combination of two reactions that both involve the use of a chiral catalyst.