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Diastereo‐ and Enantioselective Synthesis of ( E )‐δ‐Boryl‐Substituted anti ‐Homoallylic Alcohols in Two Steps from Terminal Alkynes
Author(s) -
Miura Tomoya,
Oku Naoki,
Murakami Masahiro
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201908299
Subject(s) - enantioselective synthesis , chemistry , propyne , catalysis , organic chemistry , palladium , phosphoric acid , alkyne , combinatorial chemistry
Abstract We report the highly diastereo‐ and enantioselective preparation of ( E )‐δ‐boryl‐substituted anti ‐homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)‐catalyzed 1,1‐diboration reaction of terminal alkynes with B 2 pin 2 and a palladium(I)‐mediated asymmetric allylation reaction of the resulting 1,1‐di(boryl)alk‐1‐enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.