Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

A metal-free stereoselective reductive coupling reaction between isatins and aldehydes is reported. The reaction relies on commercial diethyl phosphite (∼€70 kg(–1)) as the stoichiometric reductant. Base-catalyzed Pudovik addition and phosphonate/phosphate rearrangement achieved polarity inversion o...

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Autores principales: Horwitz, Matthew A., Tanaka, Naoya, Yokosaka, Takuya, Uraguchi, Daisuke, Johnson, Jeffrey S., Ooi, Takashi
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/PMC4618493/
https://www.ncbi.nlm.nih.gov/pubmed/26508995
http://dx.doi.org/10.1039/c5sc02170g
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author Horwitz, Matthew A.
Tanaka, Naoya
Yokosaka, Takuya
Uraguchi, Daisuke
Johnson, Jeffrey S.
Ooi, Takashi
author_facet Horwitz, Matthew A.
Tanaka, Naoya
Yokosaka, Takuya
Uraguchi, Daisuke
Johnson, Jeffrey S.
Ooi, Takashi
author_sort Horwitz, Matthew A.
collection PubMed
description A metal-free stereoselective reductive coupling reaction between isatins and aldehydes is reported. The reaction relies on commercial diethyl phosphite (∼€70 kg(–1)) as the stoichiometric reductant. Base-catalyzed Pudovik addition and phosphonate/phosphate rearrangement achieved polarity inversion on the isatin, and the derived carbanions were trapped by aldehydes with subsequent dialkoxyphosphinyl migration. Chiral iminophosphoranes were used as basic catalysts to achieve high diastereo- and enantioselectivities with excellent yields.
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spelling pubmed-46184932016-11-01 Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes Horwitz, Matthew A. Tanaka, Naoya Yokosaka, Takuya Uraguchi, Daisuke Johnson, Jeffrey S. Ooi, Takashi Chem Sci Chemistry A metal-free stereoselective reductive coupling reaction between isatins and aldehydes is reported. The reaction relies on commercial diethyl phosphite (∼€70 kg(–1)) as the stoichiometric reductant. Base-catalyzed Pudovik addition and phosphonate/phosphate rearrangement achieved polarity inversion on the isatin, and the derived carbanions were trapped by aldehydes with subsequent dialkoxyphosphinyl migration. Chiral iminophosphoranes were used as basic catalysts to achieve high diastereo- and enantioselectivities with excellent yields. Royal Society of Chemistry 2015-11-01 2015-07-30 /pmc/articles/PMC4618493/ /pubmed/26508995 http://dx.doi.org/10.1039/c5sc02170g Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Horwitz, Matthew A.
Tanaka, Naoya
Yokosaka, Takuya
Uraguchi, Daisuke
Johnson, Jeffrey S.
Ooi, Takashi
Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
title Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
title_full Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
title_fullStr Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
title_full_unstemmed Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
title_short Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
title_sort enantioselective reductive multicomponent coupling reactions between isatins and aldehydes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4618493/
https://www.ncbi.nlm.nih.gov/pubmed/26508995
http://dx.doi.org/10.1039/c5sc02170g
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