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Phosphine‐Catalyzed anti ‐Carboboration of Alkynoates with 9‐BBN‐Based 1,1‐Diborylalkanes: Synthesis and Use of Multisubstituted γ‐Borylallylboranes
Author(s) -
Yamazaki Ayaka,
Nagao Kazunori,
Iwai Tomohiro,
Ohmiya Hirohisa,
Sawamura Masaya
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712351
Subject(s) - phosphine , regioselectivity , trimethylsilyl , organocatalysis , chemistry , aldimine , acrylate , catalysis , organic chemistry , combinatorial chemistry , monomer , enantioselective synthesis , polymer
Trialkylphosphine organocatalysis has enabled the regioselective anti ‐carboboration of alkynoates with 9‐BBN‐based 1,1‐diborylalkanes to produce secondary allylboranes with β‐alkoxycarbonyl and γ‐boryl substituents. The utility of the densely functionalized allylboranes was demonstrated by the highly diastereoselective allylation of N ‐(trimethylsilyl)aldimines to produce homoallylamines containing tertiary allylborane and acrylate moieties.