Open AccessEnantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol
Author(s) -
Colton R. Davis,
Irungu K. Luvaga,
Joseph M. Ready
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c01242
Subject(s) - chemistry , stereocenter , enantioselective synthesis , stereochemistry , substitution (logic) , boronic acid , catalysis , combinatorial chemistry , organic chemistry , computer science , programming language
Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.