Copper(I)-Catalyzed Asymmetric Pinacolboryl Addition of N-Boc-imines Using a Chiral Sulfoxide-Phosphine Ligand

Ding Wang; Peng Cao; Bing Wang; Tao Jia; Yazhou Lou; Min Wang; Jian Liao

doi:10.1021/acs.orglett.5b00934

Copper(I)-Catalyzed Asymmetric Pinacolboryl Addition of N-Boc-imines Using a Chiral Sulfoxide-Phosphine Ligand

Org Lett. 2015 May 15;17(10):2420-3. doi: 10.1021/acs.orglett.5b00934. Epub 2015 Apr 23.

Authors

Ding Wang^{1

2}, Peng Cao^{1

2}, Bing Wang^{1

2}, Tao Jia^{1

2}, Yazhou Lou^{1

2}, Min Wang^{1

2}, Jian Liao^{1

2}

Affiliations

¹ Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
² University of Chinese Academy of Sciences, Beijing 100049, China.

PMID: 25906191
DOI: 10.1021/acs.orglett.5b00934

Abstract

Highly efficient and enantioselective copper(I)-catalyzed pinacolboryl addition of N-Boc-imines is reported. By using a single chiral sulfoxide-(dialkyl)phosphine (SOP) ligand, both enantiomeric isomers of α-amino boronic esters were obtained through an achiral counteranion switch.

Publication types

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

MeSH terms

Boronic Acids / chemical synthesis*
Boronic Acids / chemistry
Catalysis
Copper / chemistry*
Imines / chemistry*
Ligands
Molecular Structure
Organometallic Compounds / chemistry*
Phosphines / chemistry*
Sulfoxides / chemistry*

Substances

Boronic Acids
Imines
Ligands
Organometallic Compounds
Phosphines
Sulfoxides
Copper
phosphine