Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review

Mukaiyama aldol, Mannich, and Michael reactions are arguably amongst the most important C–C bond formation processes and enable access to highly relevant building blocks of various natural products. Their vinylogous extensions display equally high potential in the formation of important key intermed...

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Autores principales:	Leon Hoppmann, Olga García Mancheño
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	silyldienolates vinylogous reactions organocatalysis asymmetric catalysis Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/f04c25b8b859438c9a5f3f00c2204f10
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spelling	oai:doaj.org-article:f04c25b8b859438c9a5f3f00c2204f102021-11-25T18:28:17ZSilyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review10.3390/molecules262269021420-3049https://doaj.org/article/f04c25b8b859438c9a5f3f00c2204f102021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6902https://doaj.org/toc/1420-3049Mukaiyama aldol, Mannich, and Michael reactions are arguably amongst the most important C–C bond formation processes and enable access to highly relevant building blocks of various natural products. Their vinylogous extensions display equally high potential in the formation of important key intermediates featuring even higher functionalization possibilities through an additional conjugated C–C double bond. Hence, it is much desired to develop highly selective vinylogous methods in order to enable unconventional, more efficient asymmetric syntheses of biologically active compounds. In this regard, silyl-dienolates were discovered to display high regioselectivities due to their tendency toward <i>γ</i>-additions. The control of the enantio- and diastereoinduction of these processes have been for a long time dominated by transition metal catalysis, but it received serious competition by the application of organocatalytic approaches since the beginning of this century. In this review, the organocatalytic applications of silyl-dienolates in asymmetric vinylogous C–C bond formations are summarized, focusing on their scope, characteristics, and limitations.Leon HoppmannOlga García MancheñoMDPI AGarticlesilyldienolatesvinylogous reactionsorganocatalysisasymmetric catalysisOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6902, p 6902 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	silyldienolates vinylogous reactions organocatalysis asymmetric catalysis Organic chemistry QD241-441
spellingShingle	silyldienolates vinylogous reactions organocatalysis asymmetric catalysis Organic chemistry QD241-441 Leon Hoppmann Olga García Mancheño Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
description	Mukaiyama aldol, Mannich, and Michael reactions are arguably amongst the most important C–C bond formation processes and enable access to highly relevant building blocks of various natural products. Their vinylogous extensions display equally high potential in the formation of important key intermediates featuring even higher functionalization possibilities through an additional conjugated C–C double bond. Hence, it is much desired to develop highly selective vinylogous methods in order to enable unconventional, more efficient asymmetric syntheses of biologically active compounds. In this regard, silyl-dienolates were discovered to display high regioselectivities due to their tendency toward <i>γ</i>-additions. The control of the enantio- and diastereoinduction of these processes have been for a long time dominated by transition metal catalysis, but it received serious competition by the application of organocatalytic approaches since the beginning of this century. In this review, the organocatalytic applications of silyl-dienolates in asymmetric vinylogous C–C bond formations are summarized, focusing on their scope, characteristics, and limitations.
format	article
author	Leon Hoppmann Olga García Mancheño
author_facet	Leon Hoppmann Olga García Mancheño
author_sort	Leon Hoppmann
title	Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
title_short	Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
title_full	Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
title_fullStr	Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
title_full_unstemmed	Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review
title_sort	silyldienolates in organocatalytic enantioselective vinylogous mukaiyama-type reactions: a review
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/f04c25b8b859438c9a5f3f00c2204f10
work_keys_str_mv	AT leonhoppmann silyldienolatesinorganocatalyticenantioselectivevinylogousmukaiyamatypereactionsareview AT olgagarciamancheno silyldienolatesinorganocatalyticenantioselectivevinylogousmukaiyamatypereactionsareview
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Silyldienolates in Organocatalytic Enantioselective Vinylogous Mukaiyama-Type Reactions: A Review

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