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Proceedings chapter
English

Regio-, diastereo- and enantioselective carbon-carbon bond formation: recent studies and applications in organic synthesis

Published inSelectivity, a goal for synthetic efficiency, Editors Trost, Barry Martin & Bartmann, Wilhelm, p. 137-167
Presented at proceedings of the fourteenth Workshop Conference Hoechst, Schloss Reisenburg, 18-22 September 1983
PublisherWeinheim : Verlag Chemie
Publication date1984
Abstract

High π-facial stereodifferentiation is obtained on Lewis-acid-promoted Diels-Alder additions to both neopentylether-shielded acrylates (95.6 to 99.3% d.e.) and 2,3-butadienoic acid ester (99% d.e.) as used for the enantioselective synthesis of (-)-β-santalene. Similar shielding governs the 1,4-addition of nBu3P- or cyanide-stabilized MeCu·BF3 to chiral trans-enoates generating β-substituted carboxylic acids e.g. (S)-citronellic acid in 80 to 98% overall enantioselectivity. Intramolecular magnesium-ene reactions are studied and applied to the syntheses of (±)-Δ9(12)-capnellene, sinularene, 12-acetoxysinularene and khusimone. Aprotic 1,4-addition of the lithium enolate of α-methyldiphenylsilylacetate to cyclopentenone serves for a direct synthesis of methyl jasmo nate. A novel double-π-face-selective Michael addition of a neopentylether-shielded senecioate-lithium-dienolate to cyclopentenone serves for the enantioselective synthesis of (-)-khusimone.

eng
Citation (ISO format)
VON OPPOLZER, Wolfgang. Regio-, diastereo- and enantioselective carbon-carbon bond formation: recent studies and applications in organic synthesis. In: Selectivity, a goal for synthetic efficiency. Schloss Reisenburg. Weinheim : Verlag Chemie, 1984. p. 137–167.
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  • PID : unige:167999
ISBN3527261427
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