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.
Highlights
Aldol reactions are among the most prominent and most frequently applied transformations in synthetic organic chemistry because they assemble the polyketide backbone of important biologically active compounds such as antibiotics and antitumor compounds
The most frequently applied methods for aldol reactions often parallel the processes seen in the biosynthesis of polyketide natural products
Acetate or propionate units are added; subsequently, a series of further transformations are performed by large polyketide synthases to provide the substrate for the aldol reaction
Summary
Aldol reactions are among the most prominent and most frequently applied transformations in synthetic organic chemistry because they assemble the polyketide backbone of important biologically active compounds such as antibiotics and antitumor compounds. The vinylogous Mukaiyama aldol reaction (VMAR) is unique in its atom economy. Theincorporating vinylogous extension of the Mukaiyama aldol reaction allows the synthesis larger fragments while. Mukaiyama reaction is of great interest because it provides rapid access to larger carbon frameworks containing generating two new stereocenters and one double simultaneously. VMA has reactions become a general catalyst system to promote catalytic, enantioselective. In contrast to the Mukaiyama aldol reaction, its vinylogous extension, the so-called VMA. The site selectivity associated with metal dienolates can be overcome by using their by using their silyl derivatives, whose generation can be controlled by the careful choice of catalysts silyl derivatives, whose generation can be controlled byhave the careful of catalysts (promoters) and additives. Catalysis of the reaction is crucial and can proceed by two different mechanisms: (a) Aldehyde activation or (b) dienolate activation (Scheme 6).
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