Synthesis 2016; 48(16): 2553-2571
DOI: 10.1055/s-0035-1561650
short review
© Georg Thieme Verlag Stuttgart · New York

A Decade of Advance in the Asymmetric Vinylogous Mannich Reaction

María Sánchez Roselló*
a  Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain
b  Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain   Email: [email protected]   Email: [email protected]
,
Carlos del Pozo
a  Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain
,
Santos Fustero*
a  Departamento de Química Orgánica, Universidad de Valencia, 46100 Burjassot, Spain
b  Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, 46012 Valencia, Spain   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 19 April 2016

Accepted: 25 April 2016

Publication Date:
21 June 2016 (online)


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

 
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