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Silver(I)‐Catalyzed Diastereoselective Synthesis of anti ‐1,2‐Hydroxyboronates
Author(s) -
Joannou Matthew V.,
Moyer Brandon S.,
Goldfogel Matthew J.,
Meek Simon J.
Publication year - 2015
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.201507171
Subject(s) - alkyl , catalysis , activator (genetics) , aryl , chemistry , salt (chemistry) , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , gene
A catalytic protocol for the diastereoselective synthesis of anti ‐1,2‐hydroxyboronates is described. The process provides access to secondary alkyl organoborons. The deborylative 1,2‐addition reactions of alkyl 1,1‐diborons proceed in the presence of a silver(I) salt with either KO t Bu or n BuLi as an activator. The catalytic diastereoselective protocol can be extended to aryl, alkenyl, and alkyl aldehydes with up to 99:1 d.r.