Enantio-face control by molecular sieves in the asymmetric Diels-Alder reaction

S. M. Moharram, G. Hirai, K. Koyama, H. Oguri, M. Hirama

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

The presence of molecular sieves 4Å (MS 4Å) significantly influenced enantioselectivity in the Diels-Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-acetoxy-1,3-butadiene promoted by chiral TADDOL-Ti complexes. In the absence of MS 4Å the (R)-adduct was formed in 72% ee, and in the presence of MS 4Å the (S)-enantiomer in up to 53% ee. Capture of HCl by MS 4Å has been demonstrated to play a critical role. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)6669-6673
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number34
DOIs
Publication statusPublished - Aug 19 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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