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Scientific article
English

The Osmium-Catalyzed Asymmetric Dihydroxylation of cis-Fused Cyclopenteno-1,2,4-trioxanes

Published inTetrahedron Letters, vol. 35, no. 34, p. 6275-6278
Publication date1994
Abstract

Submission of racemic, cis-fused cyclopenteno-1,2,4-trioxanes (1 and 1-ent) to catalytic amounts of K₂OsO₄ and (DHQD)₂PHAL and 1.2 equivalents of N-methylmorpholine N-oxide in aqueous acetone at 20°C (hybrid AD-mix-β) for 2 h gave the (-)-enantiomer, 1-ent (ee 95%) in 30% yield. The same reaction, but with (DHQ)₂PHAL, (hybrid AD-mix-α) afforded the (+)-enantiomer, 1 (ee 95%) in 25% yield after 2.7 h reaction. Similar, efficient kinetic resolution of the racemic di-p-fluoro analogues (2 and 2-ent) was also achieved with the same reagents.

Keywords
  • Kinetic resolution
  • Double diastereoselectivity
  • 1.2-Diol
  • Dicamphanates
  • X-Ray
Funding
  • Swiss National Science Foundation - 20-38'939.93
Citation (ISO format)
JEFFORD, Charles et al. The Osmium-Catalyzed Asymmetric Dihydroxylation of <i>cis</i>-Fused Cyclopenteno-1,2,4-trioxanes. In: Tetrahedron Letters, 1994, vol. 35, n° 34, p. 6275–6278. doi: 10.1016/S0040-4039(00)73410-1
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ISSN of the journal0040-4039
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