Asymmetric Diels-Alder Reaction Catalyzed by a Chiral Titanium Reagent

Koichi Narasaka, Nobuharu Iwasawa, Masayuki Inoue, Tohru Yamada, Masako Nakashima, Jun Sugimori

Research output: Contribution to journalArticlepeer-review

328 Citations (Scopus)

Abstract

A highly enantioselective Diels-Alder reaction has been developed by employing a chiral titanium reagent generated in situ from dichlorodiisopropoxytitanium and the chiral diol 1d, which is easily derived from tartaric acid. With a catalytic amount of the titanium reagent, various acyloxazolidinone derivatives of α, β-unsaturated carboxylic acids react smoothly with dienes in the presence of 4A molecular sieves to give the corresponding optically active cycloadducts. Examination of the solvents revealed that the enantioselectivity and the reactivity of this reaction are widely dependent on the acceptor and donor properties of the solvents. By utilizing mesitylene, CFCl3, or a mixed solvent of toluene and petroleum ether (or hexane), high enantioselectivity is achieved, and various synthetically useful chiral intermediates are obtained by a simple reaction procedure.

Original languageEnglish
Pages (from-to)5340-5345
Number of pages6
JournalJournal of the American Chemical Society
Volume111
Issue number14
DOIs
Publication statusPublished - 1989 Jul
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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