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Issue 1, 2015
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Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst

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Abstract

Chiral anion phase-transfer of aryldiazonium cations was utilized to achieve highly enantioselective α-amination of carbonyl compounds. A broad scope of indanone- and benzosuberone-derived substrates was amenable to this strategy. Critical to obtaining high levels of enantioselectivity was the use of BINAM-derived phosphoric acids. The utility of this transformation was demonstrated through facile conversion of diazene products to valuable α-amino acid derivatives.

Graphical abstract: Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst

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Supplementary files

Article information


Submitted
15 Aug 2014
Accepted
18 Sep 2014
First published
02 Oct 2014

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

Chem. Sci., 2015,6, 170-173
Article type
Edge Article

Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst

H. M. Nelson, J. S. Patel, H. P. Shunatona and F. D. Toste, Chem. Sci., 2015, 6, 170
DOI: 10.1039/C4SC02494J

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