Unique stereocontrol in lanthanide(III)-catalyzed aldol reactions with the ketene silyl acetal of methyl (R)-3-hydroxybutanoate

Jin Hua Gu, Masahiro Terada, Koichi Mikami, Takeshi Nakai

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

The Eu(III)-catalyzed reaction of α-benzyloxyaldehydes with the (R)-3-hydroxybutanoate-derived ketene silyl acetal is shown to provide a higher level of both "anti" diastereofacial selection and rather unusual anti diastereoselection, compared with the conventional TiCl4-promoted version. The aldol adducts are elaborated to the carbapenem intermediates.

Original languageEnglish
Pages (from-to)1465-1468
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number11
DOIs
Publication statusPublished - 1992 Mar 10
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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