Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-isothiocyanato esters with ketones

Tatsuhiko Yoshino, Hiroyuki Morimoto, Gang Lu, Shigeki Matsunaga, Masakatsu Shibasaki

Research output: Contribution to journalArticle

103 Citations (Scopus)

Abstract

(Chemical Equation Presented) Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-substituted α-isothiocyanato esters with unactivated simple ketones is described. A Bu2Mg/Schiff base catalyst promoted the aldol addition/cyclization sequence at room temperature, giving protected α-amino-β-hydroxy esters with contiguous tetrasubstituted chiral carbon stereocenters in 99 to 68% yield, 98:2 to 74:26 dr, and 98 to 82% ee.

Original languageEnglish
Pages (from-to)17082-17083
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number47
DOIs
Publication statusPublished - Dec 2 2009

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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