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

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 o...

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Autores principales: Nelson, H. M., Patel, J. S., Shunatona, H. P., Toste, F. D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4251561/
https://www.ncbi.nlm.nih.gov/pubmed/25485073
http://dx.doi.org/10.1039/c4sc02494j
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author Nelson, H. M.
Patel, J. S.
Shunatona, H. P.
Toste, F. D.
author_facet Nelson, H. M.
Patel, J. S.
Shunatona, H. P.
Toste, F. D.
author_sort Nelson, H. M.
collection PubMed
description 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.
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spelling pubmed-42515612016-01-01 Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst Nelson, H. M. Patel, J. S. Shunatona, H. P. Toste, F. D. Chem Sci Chemistry 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. Royal Society of Chemistry 2015-01-01 2014-10-02 /pmc/articles/PMC4251561/ /pubmed/25485073 http://dx.doi.org/10.1039/c4sc02494j Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Nelson, H. M.
Patel, J. S.
Shunatona, H. P.
Toste, F. D.
Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst
title Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst
title_full Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst
title_fullStr Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst
title_full_unstemmed Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst
title_short Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst
title_sort enantioselective α-amination enabled by a binam-derived phase-transfer catalyst
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4251561/
https://www.ncbi.nlm.nih.gov/pubmed/25485073
http://dx.doi.org/10.1039/c4sc02494j
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AT tostefd enantioselectiveaaminationenabledbyabinamderivedphasetransfercatalyst

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