Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis

It is a challenging objective in synthetic organic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated into the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol r...

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Main Authors: Martin Cordes, Markus Kalesse
Format: Article
Language:English
Published: MDPI AG 2019-08-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/17/3040
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author Martin Cordes
Markus Kalesse
author_facet Martin Cordes
Markus Kalesse
author_sort Martin Cordes
collection DOAJ
description It is a challenging objective in synthetic organic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated into the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction is the most important transformation to generate this structural element as it not only creates new C−C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies of aldol and aldol-type reactions have been put forward. In this regard, the vinylogous Mukaiyama aldol reaction (VMAR) became a pivotal transformation as it allows the synthesis of larger fragments while incorporating 1,5-relationships and generating two new stereocenters and one double bond simultaneously. This review summarizes and updates methodology-oriented and target-oriented research focused on the various aspects of the vinylogous Mukaiyama aldol (VMA) reaction. This manuscript comprehensively condenses the last four years of research, covering the period 2016−2019.
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spelling doaj.art-ad894543dad84787b6679d2a55769d842022-12-21T19:54:54ZengMDPI AGMolecules1420-30492019-08-012417304010.3390/molecules24173040molecules24173040Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to SynthesisMartin Cordes0Markus Kalesse1Institute of Organic Chemistry, Gottfried Wilhelm Leibniz University of Hannover, Schneiderberg 1b, 30167 Hannover, GermanyInstitute of Organic Chemistry, Gottfried Wilhelm Leibniz University of Hannover, Schneiderberg 1b, 30167 Hannover, GermanyIt is a challenging objective in synthetic organic chemistry to create efficient access to biologically active compounds. In particular, one structural element which is frequently incorporated into the framework of complex natural products is a β-hydroxy ketone. In this context, the aldol reaction is the most important transformation to generate this structural element as it not only creates new C−C bonds but also establishes stereogenic centers. In recent years, a large variety of highly selective methodologies of aldol and aldol-type reactions have been put forward. In this regard, the vinylogous Mukaiyama aldol reaction (VMAR) became a pivotal transformation as it allows the synthesis of larger fragments while incorporating 1,5-relationships and generating two new stereocenters and one double bond simultaneously. This review summarizes and updates methodology-oriented and target-oriented research focused on the various aspects of the vinylogous Mukaiyama aldol (VMA) reaction. This manuscript comprehensively condenses the last four years of research, covering the period 2016−2019.https://www.mdpi.com/1420-3049/24/17/3040aldol reactionsMukaiyamanatural product synthesisstereoselectivityvinylogy
spellingShingle Martin Cordes
Markus Kalesse
Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
Molecules
aldol reactions
Mukaiyama
natural product synthesis
stereoselectivity
vinylogy
title Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
title_full Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
title_fullStr Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
title_full_unstemmed Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
title_short Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
title_sort very recent advances in vinylogous mukaiyama aldol reactions and their applications to synthesis
topic aldol reactions
Mukaiyama
natural product synthesis
stereoselectivity
vinylogy
url https://www.mdpi.com/1420-3049/24/17/3040
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