Chiral Thiophosphoramide and Thioamide Ligands in Catalytic Asymmetric Carbon-Carbon Bond-Formation Reactions

Wen Zhang; Min Shi

doi:10.1055/s-2006-956486

ACCOUNT

Chiral Thiophosphoramide and Thioamide Ligands in Catalytic Asymmetric Carbon-Carbon Bond-Formation Reactions

Wen Zhang, Min Shi*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Rd, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: mshi@mail.sioc.ac.cn;

Abstract

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Abstract

Metal complexes with organosulfur ligands exist widely in nature. The high polarizability of the electrons on the sulfur atoms is responsible for a variety of structures and the reactivity of metal complexes with sulfur-containing ligands. Organosulfur-containing chiral ligands have various applications in catalytic asymmetric reactions. Our group has been interested in the applications of a series of thiophosphoramide and thioamide ligands in asymmetric carbon-carbon bond-formation reactions. In this account, we describe the synthesis of chiral thiophosphoramide and thioamide ligands and their applications in catalytic asymmetric carbon-carbon bond formation.

1 Introduction

2 Synthesis of Chiral Organosulfur-Containing Ligands

3 Applications in Carbon-Carbon Bond-Formation Reactions

3.1 Conjugate Addition of Organozinc Reagents to Enones

3.2 Addition of Diethylzinc to Imines

3.3 Additon of Diethylzinc to Aldehydes

3.4 Addition of Allylic Stannane to Aldehydes

3.5 Other Applications

4 Conclusion

Key words

organosulfur-containing ligands - thiophosphoramide - thioamide - asymmetric carbon-carbon bond formation

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