Organocatalytic highly enantioselective synthesis of β-Formyl-α- hydroxyphosphonates

Sandun Perera, Vijaya Kumar Naganaboina, Long Wang, Bin Zhang*, Qunsheng Guo, Laxmidhar Rout, Cong Gui Zhao

*Corresponding author for this work

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

The cross-aldol reaction between enolizable aldehydes and α-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. β-Formyl-α- hydroxyphosphonates were obtained in high to excellent enantioselectivities. The reaction works especially well with acetaldehyde, which is a tough substrate for organocatalyzed cross-aldol reactions. The products were demonstrated to have anticancer activities.

Original languageEnglish (US)
Pages (from-to)1729-1734
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number10
DOIs
StatePublished - Jul 2011

Keywords

  • aldehydes
  • hydroxyphosphonates
  • ketophosphonates
  • organocatalysis
  • primary amines

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Organocatalytic highly enantioselective synthesis of β-Formyl-α- hydroxyphosphonates'. Together they form a unique fingerprint.

  • Cite this