Li+-Controlled Diastereoselectivity of the Addition of Allenyl Cuprate Reagents to Aldehydes

Pierre Mangeney; Hélène Gérard; Emmanuel Vrancken

doi:10.1055/s-0036-1588613

Synthesis, Table of Contents

Synthesis 2017; 49(03): 526-531
DOI: 10.1055/s-0036-1588613

short review

Li⁺-Controlled Diastereoselectivity of the Addition of Allenyl Cuprate Reagents to Aldehydes

Pierre Mangeney

^aLaboratoire de Chimie Organique, UMR 7611 Institut de Chimie Moléculaire, FR 2769, UPMC - Univ. Paris 06, CNRS, case 43, 4 Place Jussieu, 75262 Paris Cedex 05, France

,

Hélène Gérard

^bSorbonne Universités, UPMC Univ Paris 06, CNRS, UMR 7616, Laboratoire de Chimie Théorique, 75005 Paris, France

,

Emmanuel Vrancken*

^cInstitut Charles Gerhardt Montpellier, UMR 5253, CNRS-UM-ENSCM, 8, rue de l’école Normale, 34296 Montpellier, France Email: emmanuel.vrancken@enscm.fr

› Author Affiliations

Abstract

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In memory of Professor Jean Normant, with deepest respect and gratitude.

Abstract

This personal account summarizes our recent work regarding the addition of allenyl cuprates to aldehydes. An intertwined experimental and theoretical study enables highlighting of the crucial role of Li⁺ as a structuring agent in the different intermediates and transition states involved, and thus on the diastereochemical outcome of the reaction.

1 Introduction

2 Results and Discussion

3 Conclusion

Key words

homopropargylic alcohols - allene - cuprate - lithium - diastereoselectivity - DFT calculations

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References

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