Asymmetric Intramolecular Ene Reaction Catalyzed by a Chiral Titanium Reagent and Synthesis of (—)‐ε‐Cadinene

Koichi Narasaka, Yujiro Hayashi, Satoru Shimada, Jun Yamada

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

A highly diastereo‐ and enantio‐selective intramolecular ene reaction was developed by employing a chiral titanium reagent generated in situ from TiCl2(OPri)2 and a tartrate‐derived chiral 1,4‐diol. This reaction afforded masked cyclohexanone and cyclopentanone derivatives with high optical purities which were synthetically useful chiral building blocks. From the intramolecular ene product (—)‐ε‐cadinene was synthesized by the use of the newly developed intramolecular Michael reaction.

Original languageEnglish
Pages (from-to)261-271
Number of pages11
JournalIsrael Journal of Chemistry
Volume31
Issue number3
DOIs
Publication statusPublished - 1991
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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