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Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid

We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5...

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Autores principales: Yang, Xiaoyu, Toste, F. Dean
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5155590/
https://www.ncbi.nlm.nih.gov/pubmed/27990248
http://dx.doi.org/10.1039/c5sc04202j
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author Yang, Xiaoyu
Toste, F. Dean
author_facet Yang, Xiaoyu
Toste, F. Dean
author_sort Yang, Xiaoyu
collection PubMed
description We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5- and 1,4-ketoaldehyde derivatives, which are both important building blocks in organic synthesis.
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spelling pubmed-51555902016-12-14 Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid Yang, Xiaoyu Toste, F. Dean Chem Sci Chemistry We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5- and 1,4-ketoaldehyde derivatives, which are both important building blocks in organic synthesis. Royal Society of Chemistry 2016-04-01 2016-01-19 /pmc/articles/PMC5155590/ /pubmed/27990248 http://dx.doi.org/10.1039/c5sc04202j Text en This journal is © The Royal Society of Chemistry 2016 https://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
Yang, Xiaoyu
Toste, F. Dean
Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
title Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
title_full Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
title_fullStr Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
title_full_unstemmed Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
title_short Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
title_sort asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5155590/
https://www.ncbi.nlm.nih.gov/pubmed/27990248
http://dx.doi.org/10.1039/c5sc04202j
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AT tostefdean asymmetricadditionofabranchedcyclicketonestoallenamidescatalyzedbyachiralphosphoricacid