A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon

Fengrui Lang, Daniel Zewge, Zhiguo J. Song, Mirlinda Biba, Peter Dormer, David Tschaen, R. P. Volante, Paul J. Reider

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

A highly stereoselective aldol reaction was observed on chromane carboxylate ester 1 via the corresponding diisopinocampheyl boron-enolate using commercially available (-)-DIP-Cl reagent. The aldol product 2c was obtained in 89% yield with 48 dr and 92% ee. Further studies indicate that stereoselective formation of the enolate and proper chiral ligand on boron are responsible for the exceptional diastereo- and enantioselectivity in the aldol reaction.

Original languageEnglish (US)
Pages (from-to)5285-5288
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number28
DOIs
StatePublished - Jul 7 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'A stereoselective aldol reaction via diisopinocampheyl boron-enolate in preparation of chromane carboxylate with quaternary carbon'. Together they form a unique fingerprint.

  • Cite this