Novel Amino Acid Based Bifunctional
Chiral Phosphines

Su-Xi Wang; Xiaoyu Han; Fangrui Zhong; Youqing Wang; Yixin Lu

doi:10.1055/s-0031-1289538

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Synlett 2011(19): 2766-2778
DOI: 10.1055/s-0031-1289538

ACCOUNT

Novel Amino Acid Based Bifunctional Chiral Phosphines

Su-Xi Wang, Xiaoyu Han, Fangrui Zhong, Youqing Wang, Yixin Lu*
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Republic of Singapore
Fax: +6567791691; e-Mail: chmlyx@nus.edu.sg;

Further Information

Publication History

Received 9 June 2011
Publication Date:
19 October 2011 (online)

Abstract
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Abstract

As a significant complement to amino catalysts, phosphines are versatile Lewis base catalysts capable of promoting a wide range of diverse organic transformations. In particular, chiral phosphines bearing a Brønsted acid moiety have recently emerged as powerful bifunctional phosphine catalysts in asymmetric synthesis and catalysis. In this account, we document our recent efforts on the design and development of novel amino acid/dipeptide-based bifunctional chiral phosphines, and their applications in enantioselective (aza)-Morita-Baylis-Hillman (MBH) reactions and [3+2]-cycloaddition reactions.

1 Introduction

2 Bifunctional Phosphine Catalysis

3 Novel Amino Acid Based Bifunctional Chiral Phosphines

3.1 Design of Amino Acid Derived Phosphines

3.2 Threonine Core as the Chiral Scaffold

3.3 Aza-MBH Reaction Promoted by Phosphine-Sulfonamide Catalysts

3.4 MBH Reaction Catalyzed by Phosphine-Thioureas

3.5 [3+2] Cycloadditions of Allenoates to Acrylates/Acrylamides Promoted by Dipeptide-Derived Phosphines

3.6 [3+2] Cycloaddition of the MBH Adducts Catalyzed by Phosphine-Τhioureas

4 Conclusion and Outlook

Key words

amino acids - chiral phosphines - bifunctional catalysts - aza-Morita-Baylis-Hillman reaction - [3+2] cycloaddition

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