Synlett
DOI: 10.1055/s-0036-1589080
letter
© Georg Thieme Verlag Stuttgart · New York

Chiral Phosphinyl Enamines and Their Asymmetric Reduction through Group-Assisted Purification Chemistry Leading to Enantiopure β-Amino Esters/Amides

Shuo Qiaoa, Jianbin Wua, b, Junming Moa, Preston T. Spigenera, Brian Nlong Zhaoc, Bo Jiang*a, d, Guigen Li*a, b
  • aDepartment of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA   Email: guigen.li@ttu.edu
  • bInstitute of Chemistry and Biomedical Sciences (ICBMS), Nanjing University, Nanjing 210093, P. R. of China
  • cShanghai High School International Division, No. 989, Baise Road, Shanghai 200231, P. R. of China
  • dSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. China   Email: jiangchem@jsnu.edu.cn
We would like to acknowledge financial support from the National Natural Science Foundation of China (No. 21332005, 21672100) and the Robert Welch Foundation (D-1306).
Further Information

Publication History

Received: 11 May 2017

Accepted after revision: 26 June 2017

Publication Date:
04 August 2017 (eFirst)

Abstract

A series of new chiral N-phosphinyl β-enamino esters and amides were successfully prepared with excellent Z-stereoselectivity (Z/E > 99:1 in nearly all cases). Group-assisted purification chemistry proved to be an efficient method for the asymmetric reduction of the resulting β-enamino esters/amides to give enantiopure β-amino esters/amides. The asymmetric reduction can be controlled efficiently by using a combination of sodium cyanoborohydride and acetic acid.

Supporting Information