Cu-Catalyzed SN2' Substitution of Propargylic Phosphates with Vinylarene-Derived Chiral Nucleophiles: Synthesis of Chiral Allenes

Bing Wang; Xihong Wang; Xuemei Yin; Wangzhi Yu; Yang Liao; Jialin Ye; Min Wang; Jian Liao

doi:10.1021/acs.orglett.9b00908

Cu-Catalyzed S_N2' Substitution of Propargylic Phosphates with Vinylarene-Derived Chiral Nucleophiles: Synthesis of Chiral Allenes

Org Lett. 2019 Jun 7;21(11):3913-3917. doi: 10.1021/acs.orglett.9b00908. Epub 2019 May 10.

Authors

Bing Wang^{1

2}, Xihong Wang^{1

2}, Xuemei Yin^{1

2}, Wangzhi Yu^{1

2}, Yang Liao^{1

2}, Jialin Ye³, Min Wang^{1

2}, Jian Liao^{1

2

3}

Affiliations

¹ Chengdu Institute of Biology , Chinese Academy of Sciences , Chengdu 610041 , China.
² University of Chinese Academy of Sciences , Beijing 100049 , China.
³ College of Chemical Engineering , Sichuan University Chengdu 610065 , China.

PMID: 31074282
DOI: 10.1021/acs.orglett.9b00908

Abstract

A new Cu-catalyzed enantioselective three-component (i.e., styrenes, B₂pin₂, and propargylic phosphates) allenylation via an S_N2' substitution of propargylic electrophiles with vinylarene-derived chiral nucleophiles is presented. This method provides an efficient and enantioselective approach to access a range of optically pure di-(1,1-), tri-, and tetra-substituted allenes with α-central chirality and axial chirality in excellent chemo-, regio-, diastereo-, and enantioselectivities.

Publication types

Research Support, Non-U.S. Gov't