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 avq 2014
Accepted
18 sen 2014
First published
02 okt 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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