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Synthesis of β‐Boryl‐α‐Aminosilanes by Copper‐Catalyzed Aminoboration of Vinylsilanes
Author(s) -
Kato Kodai,
Hirano Koji,
Miura Masahiro
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.201608139
Subject(s) - regioselectivity , chemistry , stereospecificity , copper , catalysis , group (periodic table) , functional group , combinatorial chemistry , stereochemistry , organic chemistry , polymer
A copper‐catalyzed regioselective and stereospecific aminoboration of vinylsilanes with bis(pinacolato)diboron (pinB‐Bpin) and hydroxylamines has been developed. In the presence of a CuCl/MeO‐dppbz catalyst, the boryl group and amino group are incorporated at the β position and α position, respectively, and the corresponding β‐boryl‐α‐aminosilanes are obtained with good diastereoselectivity. The boryl group is a good latent functional group, and subsequent manipulations provide a variety of β‐functionalized α‐aminosilanes of great potential in medicinal chemistry. Additionally, preliminary application to asymmetric catalysis is also described.