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

Shuo Qiao, Jianbin Wu, Junming Mo, Preston T. Spigener, Brian Nlong Zhao, Bo Jiang, Guigen Li

Research output: Contribution to journalArticle

8 Scopus citations

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.

Original languageEnglish
Pages (from-to)2483-2488
Number of pages6
JournalSynlett
Volume28
Issue number18
DOIs
StatePublished - Nov 13 2017

Keywords

  • amino amides
  • amino esters
  • asymmetric reduction
  • group-assisted purification
  • phosphinyl enamines

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