Details
| Original language | English |
|---|---|
| Article number | 3040 |
| Journal | MOLECULES |
| Volume | 24 |
| Issue number | 17 |
| Early online date | 22 Aug 2019 |
| Publication status | Published - 1 Sept 2019 |
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.
Keywords
- Aldol reactions, Mukaiyama, Natural product synthesis, Stereoselectivity, Vinylogy
ASJC Scopus subject areas
- Chemistry(all)
- Analytical Chemistry
- Chemistry(all)
- Chemistry (miscellaneous)
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Medicine
- Pharmacology, Toxicology and Pharmaceutics(all)
- Pharmaceutical Science
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: MOLECULES, Vol. 24, No. 17, 3040, 01.09.2019.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
AU - Cordes, Martin
AU - Kalesse, Markus
PY - 2019/9/1
Y1 - 2019/9/1
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.
AB - 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.
KW - Aldol reactions
KW - Mukaiyama
KW - Natural product synthesis
KW - Stereoselectivity
KW - Vinylogy
UR - http://www.scopus.com/inward/record.url?scp=85071477227&partnerID=8YFLogxK
U2 - 10.3390/molecules24173040
DO - 10.3390/molecules24173040
M3 - Article
C2 - 31443344
AN - SCOPUS:85071477227
VL - 24
JO - MOLECULES
JF - MOLECULES
SN - 1420-3049
IS - 17
M1 - 3040
ER -