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Hexahydropyrrolo[2,3‐ b ]indoles: A New Class of Structurally Rigid Tricyclic Skeleton for Oxazaborolidine‐Catalyzed Asymmetric Borane Reduction
Author(s) -
Xiao Jian,
Wong Zhen Zhou,
Lu Yun Peng,
Loh Teck Peng
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900908
Subject(s) - chemistry , enantioselective synthesis , borane , tricyclic , catalysis , reduction (mathematics) , indole test , skeleton (computer programming) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , geometry , mathematics , computer science , programming language
A new class of structurally rigid tricyclic chiral ligands based on the hexahydropyrrolo[2,3‐ b ]indole skeleton has been rationally designed and the catalytic abilities in asymmetric catalysis have been shown in the enantioselective borane reduction of prochiral ketones to afford the chiral alcohols in excellent yields and high enantioselectivities (up to 97% ee ).