Synthesis 2020; 52(02): 189-196
DOI: 10.1055/s-0039-1690713
short review
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Preparation and Reactions of Chiral Secondary Alkyllithiums

Juri Skotnitzki
,
Alexander Kremsmair
,
Paul Knochel
Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstr. 5-13, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
› Author Affiliations
We thank the SFB 749 for financial support. J.S. thanks the FCI foundation for a fellowship.
Further Information

Publication History

Received: 16 September 2019

Accepted after revision: 20 September 2019

Publication Date:
08 October 2019 (online)


In memory of Prof. Dr. Dieter Enders

Abstract

The preparation of chiral non-stabilized open-chain alkyl­lithium reagents prepared from the corresponding chiral secondary alkyl iodides and their subsequent transmetalation to the corresponding secondary alkylcopper or alkylzinc derivatives is reviewed. These new organometallic reagents allow the stereoselective preparation of a broad range of chiral molecules.

1 Introduction

2 Stereoselective Preparation of Secondary Alkyllithiums

3 Preparation of Stereodefined Secondary Alkylcopper Reagents

4 Preparation of Stereodefined Secondary Alkylzinc Derivatives and Their Stereoselective Cross-Coupling with Alkenyl and Aryl Halides­

5 Conclusion