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. 2018 Apr 6;8(4):2897-2901.
doi: 10.1021/acscatal.8b00221. Epub 2018 Feb 23.

Enantioselective Synthesis of Nonracemic Geminal Silylboronates by Pt-Catalyzed Hydrosilylation

Adam A Szymaniak, Chenlong Zhang, John R Coombs, James P Morken

Enantioselective Synthesis of Nonracemic Geminal Silylboronates by Pt-Catalyzed Hydrosilylation

Adam A Szymaniak et al. ACS Catal. .

Abstract

A Pt-catalyzed enantioselective hydrosilylation of alkenylboronates is described. This reaction occurs with high regio- and enantioselectivity, providing a convenient route to chiral non-racemic geminal silylboronates. These compounds are useful reagents in stereoselective synthesis.

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Figures

Figure 1.
Figure 1.
a: Direct transformation of silylboronate to chiral silyl alcohol, silyl amine, and vicinal silylboronate. b: Telescope sequence from vicinal silylboronate to oxazolidinone by amination and oxidation.
Figure 2.
Figure 2.
Single-flask sequential catalytic alkyne hydroboration/hydrosilylation/amination for the synthesis of silylamine 20 from 3-phenyl-1-propyne.
Figure 3.
Figure 3.
Large-scale, dry-box-free enantioselective platinum-catalyzed hydrosilylation.
Figure 4.
Figure 4.
Regioselectivity of the deuteriosilylation of a vinyl boronate under Pt-phosphoramidite catalysis.
Scheme 1.
Scheme 1.
Utility and Previous Catalytic Syntheses of Nonracemic Geminal Dimetallic Reagents
See this image and copyright information in PMC

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