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Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis.
Molecules. 2019 Aug 22; 24(17)M

Abstract

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.

Authors+Show Affiliations

Institute of Organic Chemistry, Gottfried Wilhelm Leibniz University of Hannover, Schneiderberg 1b, 30167 Hannover, Germany.Institute of Organic Chemistry, Gottfried Wilhelm Leibniz University of Hannover, Schneiderberg 1b, 30167 Hannover, Germany. markus.kalesse@oci.uni-hannover.de.

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

31443344

Citation

Cordes, Martin, and Markus Kalesse. "Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis." Molecules (Basel, Switzerland), vol. 24, no. 17, 2019.
Cordes M, Kalesse M. Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis. Molecules. 2019;24(17).
Cordes, M., & Kalesse, M. (2019). Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis. Molecules (Basel, Switzerland), 24(17). https://doi.org/10.3390/molecules24173040
Cordes M, Kalesse M. Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis. Molecules. 2019 Aug 22;24(17) PubMed PMID: 31443344.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis. AU - Cordes,Martin, AU - Kalesse,Markus, Y1 - 2019/08/22/ PY - 2019/06/25/received PY - 2019/08/15/revised PY - 2019/08/19/accepted PY - 2019/8/25/entrez PY - 2019/8/25/pubmed PY - 2020/1/22/medline KW - Mukaiyama KW - aldol reactions KW - natural product synthesis KW - stereoselectivity KW - vinylogy JF - Molecules (Basel, Switzerland) JO - Molecules VL - 24 IS - 17 N2 - 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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/31443344/Very_Recent_Advances_in_Vinylogous_Mukaiyama_Aldol_Reactions_and_Their_Applications_to_Synthesis_ DB - PRIME DP - Unbound Medicine ER -