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Enantioselective Catalysts for the Synthesis of α‐Substituted Allylboronates—An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols
Author(s) -
Brauns Marcus,
Muller Frédéric,
Gülden Daniel,
Böse Dietrich,
Frey Wolfgang,
Breugst Martin,
Pietruszka Jörg
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.201509198
Subject(s) - enantioselective synthesis , catalysis , chemistry , functional group , combinatorial chemistry , protecting group , reaction conditions , organic chemistry , alkyl , polymer
The use of a convenient protecting group for boronates allows a selective, catalyzed S N 2′ reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.