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Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu−H‐Catalyzed Si−O Coupling
Author(s) -
Seliger Jan,
Dong Xichang,
Oestreich Martin
Publication year - 2019
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.201813229
Subject(s) - kinetic resolution , enantioselective synthesis , chemistry , aryl , alkyl , catalysis , reagent , alkyne , silylation , selectivity , combinatorial chemistry , surface modification , organic chemistry
A broad range of tertiary propargylic alcohols were kinetically resolved by catalyst‐controlled enantioselective silylation. This non‐enzymatic kinetic resolution is catalyzed by a Cu−H species and makes use of the commercially available precatalyst MesCu/( R , R )‐Ph‐BPE and a simple hydrosilane as the resolving reagent. Both alkyl,aryl‐ as well as dialkyl‐substituted propargylic alcohols participate, and especially high selectivity factors are achieved when the alkyne terminus carries a TIPS group, which also enables facile post‐functionalization in this position ( s up to 207).
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