Synthesis 2019; 51(09): 1923-1934
DOI: 10.1055/s-0037-1611743
short review
© Georg Thieme Verlag Stuttgart · New York

Acyl Transfer Strategies as Transient Activations for Enantioselective Synthesis

Jean Rodriguez
,
Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France   Email: adrien.quintard@univ-amu.fr
› Author Affiliations
The Centre National de la Recherche Scientifique (CNRS) and Aix-Marseille Université are gratefully acknowledged for financial support.
Further Information

Publication History

Received: 16 January 2019

Accepted after revision: 29 January 2019

Publication Date:
14 March 2019 (eFirst)

Dedicated to Michel Quintard on the occasion of his retirement

Abstract

In order to circumvent reactivity or selectivity issues associated with the addition of enolates to electrophiles, chemists have devised innovative methods involving transient activating groups. One of these powerful methods consists of the use of activated ketones, such as α-nitroketones, β-dicarbonyl compounds or β-ketosulfones, with electrophiles possessing a latent hydroxy or amine function. In the presence of a suitable catalyst, an enantioselective addition to the electrophile is facilitated triggering a subsequent Claisen-type fragmentation resulting in an acyl transfer. This subsequent step unveils the desired mono-activated function while directly transferring the ketone, forming in situ on the other side an ester or an amide.

1 Introduction

2 Intramolecular Acyl Transfer with Acyclic Substrates

2.1 Bifunctional Catalysis

2.2 Aminocatalysis

3 Intermolecular Acyl Transfer with Acyclic Substrates

4 Medium-Sized-Ring Formation with Cyclic Substrates

5 Conclusion

 
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