Stereo and reg ioselective openings of chiral 2,3-epoxy alcohols. versatile routes to optically pure natural products and drugs. unusual kinetic resolutions

K. Barry Sharpless, Carl H. Behrens, Tsutomu Katsuki, Albert W M LEE, Victor S. Martin, Muneo Takatani, Steven M. Viti, Frederick J. Walker, Scott S. Woodard

Research output: Contribution to journalArticlepeer-review

255 Citations (Scopus)

Abstract

A diverse selection of new synthetic applications of the titanium-catalyzed asymmetric epoxidation (AE) process is described. These include asymmetric syntheses of (+)-Darvon Alcohol, (-)-bestatin, (+)-2-methyl bestatin, (-)-propranolol, (-)-α-amino-β-hydroxybutyric acid, and (-)- and (+)-frontal in. The kinetic resolution mode of the AE process was used to prepare chiral insect pheromones in very high (>99% e.e.) optical purity; these include (+)-and (-)-a-caprolactone, (-)-exobrevicomin, (-)-endobrevi-comin, (+)-and (-)-ipsdienol, and (+)-trans-verbenol. A number of unusual kinetic resolutions based on the AE process are presented; these include resolutions of allenic alcohols, α-acetylenic carbinols, β-hydroxy sulfides, and a dienol.

Original languageEnglish
Pages (from-to)589-604
Number of pages16
JournalPure and Applied Chemistry
Volume55
Issue number4
DOIs
Publication statusPublished - Jan 1983

Scopus Subject Areas

  • Chemistry(all)
  • Chemical Engineering(all)

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