Acyclic Amino Acid Based Bifunctional Chiral Tertiary Amines, Quaternary Ammoniums and Iminophosphoranes as Organo­catalysts

Abstract

Acyclic amino acids are one of the most ideal chiral scaffolds for the construction of organocatalysts. The development of acyclic amino acid based bifunctional chiral tertiary amines and their powerful catalytic abilities have been demonstrated in many asymmetric reactions. In this account, we summarize asymmetric transformations promoted by bifunctional chiral tertiary amines according to reaction patterns. Moreover, asymmetric reactions mediated by acyclic amino acid derived quaternary ammoniums as phase-transfer catalysts, and acyclic amino acid derived iminophosphoranes as bifunctional superbases are discussed.

1 Introduction

2 Acyclic Amino Acid Derived Chiral Tertiary Amines (CTAs)

2.1 CTA-Catalyzed Asymmetric Conjugate Addition Reactions

2.2 CTA-Catalyzed Asymmetric Aldol Reactions

2.3 CTA-Catalyzed Asymmetric Mannich Reactions

2.4 CTA-Catalyzed Asymmetric Tandem Reactions

3 Acyclic Amino Acid Derived Chiral Quaternary Ammoniums

4 Acyclic Amino Acid Derived Chiral Iminophosphoranes

5 Conclusion and Outlook

Key words

acyclic amino acids - tertiary amines - quaternary ammonium salts - iminophosphoranes - bifunctional catalysts

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