Sugarometallic chemistry: Aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction

Tony K.M. Shing, Hak Fun Chow, Ivan H.F. Chung

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

The diastereoselectivity of the Diels-Alder reaction of η6-(4'-methylbenzyl 2-O-Acryloyl-3,4-O-isopropylidene-β-L-arabinopyranoside) tricarbonylchromium(0) 5 with isoprene, butadiene, cyclopentadiene, and furan were studied, and the best selectivity was 95:5 (with isoprene), whereas the diastereoselectivity of the same reaction with the noncomplexed chiral auxiliary-acrylate 6 was only 78:22. The absolute configuration of the newly generated stereogenic center was found to be R in each case.

Original languageEnglish
Pages (from-to)3713-3716
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number21
DOIs
Publication statusPublished - 1996 May 2

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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