Issue 1, 2015

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 8 2014
Accepted
18 9 2014
First published
02 10 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 170-173

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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