Chiral N-phosphonyl imine chemistry: Asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines

Teng Ai, Suresh Pindi, Padmanabha V. Kattamuri, Guigen Li

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Diphenyl diamine-based phosphonyl imines attached by the N-isopropyl group in the auxiliary have been synthesized in good yields under convenient reaction conditions. These new chiral N-phosphonyl imines can react with glycine enolate smoothly to give chiral α-β diamino esters in good yields (72%-90%) and up to excellent diastereoselectivity (>99:1 dr). By treatment with HBr, the chiral auxiliary can be readily removed. The absolute structure has been unambiguously determined by converting a product to a known sample.

Original languageEnglish (US)
Pages (from-to)125-129
Number of pages5
JournalScience China Chemistry
Volume53
Issue number1
DOIs
StatePublished - Jan 2010

Bibliographical note

Funding Information:
This work was supported by the National Institutes of Health (Grant Nos. 1 RO3 DA026960-01), and Robert Welch Foundation (Grant No. D-1361)

Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.

Keywords

  • Chiral N-phosphonyl imine
  • Chiral phosphoramide
  • Glycine enolate
  • α-β diamino ester

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