Diastereoselective cyanation of α-keto amides derived from N-phenyl camphorpyrazolidinone and camphorsultam

Hua Lin Hsu, Hsin Ling Wu, Uppala Venkatesham, Kwun Min Chen

Research output: Contribution to journalArticle

Abstract

The diastereoselective cyanation of α-keto amides using trimethylsilyl cyanide in the presence of a Lewis acid is described. The corresponding O-acetylated cyanohydrins are obtained in good to high levels of stereoselectivities. The predominance of products with the S absolute configuration at the newly generated stereogenic center was deduced from single crystal X-ray analysis. 13C NMR data suggest that a preferential s-cis conformation was formed by the chelation of a Lewis acid to the dicarbonyl oxygen atoms.

Original languageEnglish
Pages (from-to)448-454
Number of pages7
JournalJournal of the Chinese Chemical Society
Volume53
Issue number2
Publication statusPublished - 2006 Apr 1

Keywords

  • Chiral auxiliary
  • Cyanation
  • Diastereoselective
  • Lewis acid
  • Timethylsilyl cyanide
  • α-ketoamides

ASJC Scopus subject areas

  • Chemistry(all)

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