The Osmium-Catalyzed Asymmetric Dihydroxylation of <i>cis</i>-Fused Cyclopenteno-1,2,4-trioxanes

Article Article scientifique Article The Osmium-Catalyzed Asymmetric Dihydroxylation of <i>cis</i>-Fused Cyclopenteno-1,2,4-trioxanes eng 1994 author Jefford Charles 24934 author Misra Dharmendra 26901 author Dishington Allan Paul 28874 author Timari Geza 29815 author Rossier Jean-Claude 25984 author Bernardinelli Gérald Hugues 24765 6275-6278 10.1016/S0040-4039(00)73410-1 0040-4039 https://linkinghub.elsevier.com/retrieve/pii/S0040403900734101 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. Kinetic resolution Double diastereoselectivity 1.2-Diol Dicamphanates X-Ray Dewey 540 Swiss National Science Foundation 20-38'939.93 CH 36 Département de chimie organique 141 false Tetrahedron Letters 35 34 c3ba177f-4a1a-4b5a-b9fc-4eb6c99df59b Article (Published version) Restricted Jefford_TL_1994356275.pdf 1394057 application/pdf Vignette Public 1-s2.0-S0040403900734101-gr1.gif 2782 image/gif restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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The Osmium-Catalyzed Asymmetric Dihydroxylation of cis-Fused Cyclopenteno-1,2,4-trioxanes	Tetrahedron Letters			1994	197	0

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Dishington, Allan Paul