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Issue 26, 2019
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Highly diastereoselective preparation of chiral NHC-boranes stereogenic at the boron atom

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Abstract

Stereogenic main group elements are clearly generating interest in the enantioselective catalysis field. Surprisingly, while chiral organoboron reagents are very useful in stereoselective transformations, few scaffolds stereogenic at boron and configurationally stable have been reported to date. Herein, we describe an original library of chiral NHC-boranes, stereogenic at the boron atom, that has been prepared in only a few steps and in good yields (up to 93%). Key steps involve a chlorination/arylation sequence in the presence of simple Grignard reagents from bicyclic NHC-boranes. The high and unprecedented diastereoselectivity observed during the second step (up to 99 : 1 dr) has been rationalized through a plausible SRN1 mechanism thanks to EPR observations and DFT calculations.

Graphical abstract: Highly diastereoselective preparation of chiral NHC-boranes stereogenic at the boron atom

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Article information


Submitted
25 Mar 2019
Accepted
23 May 2019
First published
24 May 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 6524-6530
Article type
Edge Article

Highly diastereoselective preparation of chiral NHC-boranes stereogenic at the boron atom

C. Aupic, A. Abdou Mohamed, C. Figliola, P. Nava, B. Tuccio, G. Chouraqui, J. Parrain and O. Chuzel, Chem. Sci., 2019, 10, 6524
DOI: 10.1039/C9SC01454C

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