A Decade of Advance in the Asymmetric Vinylogous Mannich Reaction

María Sánchez Roselló; Carlos del Pozo; Santos Fustero

doi:10.1055/s-0035-1561650

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(16): 2553-2571
DOI: 10.1055/s-0035-1561650

short review

A Decade of Advance in the Asymmetric Vinylogous Mannich Reaction

María Sánchez Roselló*

^aDepartamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain

^bLaboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain eMail: maria.sanchez-rosello@uv.es eMail: santos.fustero@uv.es

,

Carlos del Pozo

^aDepartamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain

,

Santos Fustero*

^aDepartamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain

^bLaboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain eMail: maria.sanchez-rosello@uv.es eMail: santos.fustero@uv.es

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Abstract

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Abstract

When the principle of vinylogy is applied to imines as electrophiles, the so-called vinylogous Mannich reaction (VMR), γ-aminocarbonyl (such as butenolides) and β-aminocarbonyl compounds are generated in a very efficient manner. The asymmetric version of this vinylogous Mannich reaction gives access to highly functionalized chiral synthons, which are suitable for further transformations. The versatility of this methodology is exemplified with the synthesis of several alkaloids and natural products.

1 Introduction

2 Asymmetric Vinylogous Mannich Reactions (VMR) with 2-Silyloxyfurans and 2-Silyloxypyrroles

3 Asymmetric VMR with Acyclic Silyl Dienolates and Silyl Dienol Ketene Acetals

4 Asymmetric VMR with γ-Butenolides and γ-Butyrolactams

5 Asymmetric VMR with α,α-Dicyanoolefins

6 Miscellaneous Donors in Asymmetric VMR

7 Application of the VMR to Natural Product Synthesis

8 Conclusions

Key words

vinylogous - Mannich reaction - asymmetric synthesis - γ-aminocarbonyl compounds - dienolates

Volltext

Referenzen

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