A Decade of Advance in the Asymmetric Vinylogous Mannich Reaction

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

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