Enantio- and diastereoselective construction of vicinal quaternary and tertiary carbon centers by catalytic Michael reaction of α-substituted β-keto esters to cyclic enones

Keisuke Majima, Shin Ya Tosaki, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A catalytic enantio- and diastereoselective Michael reaction was achieved to construct vicinal quaternary and tertiary carbon centers in one step. Using 5 mol % of La(O-i-Pr)3 and 10 mol % of a new N-linked-BINOL type ligand, the reaction of α-substituted β-keto esters to cyclic enones provided the corresponding Michael adducts in up to quantitative yield with a diastereomeric ratio up to 86/14 and enantiomeric excess up to 86% for the major isomer. An alternative catalyst preparation method using La(OTf)3 instead of La(O-i-Pr)3 was also examined.

Original languageEnglish
Pages (from-to)5377-5381
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number32
DOIs
Publication statusPublished - Aug 8 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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