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Copper‐Catalyzed Regio‐ and Enantioselective Aminoboration of Unactivated Terminal Alkenes
Author(s) -
Kato Kodai,
Hirano Koji,
Miura Masahiro
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801070
Subject(s) - enantioselective synthesis , regioselectivity , chemistry , enantiomer , catalysis , copper , organic chemistry , enantiomeric excess , stereoisomerism , stereochemistry , combinatorial chemistry
A CuCl/( R , R )‐PTBP‐BDPP‐catalyzed regioselective and enantioselective aminoboration of simple and unactivated terminal alkenes with bis(pinacolato)diboron (pinB‐Bpin) and hydroxylamines has been developed. The amino group and boryl group were incorporated at the internal position and terminal position, respectively, and the corresponding chiral β‐borylalkylamines were obtained with good to high enantiomeric ratios. The asymmetric copper catalysis allows rapid and concise transformation of readily available olefinic feedstock‐like materials into functionalized chiral alkylamines of high potential in medicinal and pharmaceutical chemistry.