Stereoselective Preparation and Reactions of Chiral Secondary Alkyllithiums

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

Key words

lithium - stereoselective - copper - zinc - cross-coupling - natural­ products

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