Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Yiwen Xiong, Haibo Mei, Lingmin Wu, Jianlin Han, Yi Pan, Guigen Li

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A variety of chiral N-phosphinyl a-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected a-amino esters. The reduction proceeded very well with excellent chemical yields (88-98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.

Original languageEnglish
Pages (from-to)653-659
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
StatePublished - Mar 13 2014

Keywords

  • Group-assisted purification
  • Phosphinyl auxiliary
  • Reduction
  • α-amino ester
  • α-imino ester

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