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

Creators: Nelson, H. M.; Patel, J. S.; Shunatona, H. P.; Toste, F. D.

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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.

Additional Information

© 2015 The Author(s). This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. All publication charges for this article have been paid for by the Royal Society of Chemistry. Submitted 15 Aug 2014; Accepted 18 Sep 2014; First published 02 Oct 2014. This article is part of the themed collection: Celebrating our 2018 prize and award winners. We gratefully acknowledge NIHGMS (R01 GM104534) for financial support. H.M.N. would like to acknowledge the UNCF and Merck for generous funding. We would also like to thank Dr Matthew Winston for useful discussion regarding ¹⁵N labeling and acknowledge the College of Chemistry CheXray (NIH Shared Instrumentation Grant S10-RR027172) and Antonio DiPasquale for X-ray crystallographic data.

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