Studies on an Oxidative 1,4-Addition to s-trans-1,3-Dienes, a Key Reaction in a Strigol Total Synthesis
Oxidation of 4,6‐heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5‐(3‐hydroxypropenyl)dihydrofuran‐2‐one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six‐memb...
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| Published in | European journal of organic chemistry Vol. 2003; no. 23; pp. 4640 - 4653 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.12.2003
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1434-193X 1099-0690 |
| DOI | 10.1002/ejoc.200200671 |
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| Abstract | Oxidation of 4,6‐heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5‐(3‐hydroxypropenyl)dihydrofuran‐2‐one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six‐membered ring as part of the s‐trans‐diene system was an intermediate in a strigol total synthesis; a second system lacking the six‐membered ring is the subject of the present publication. We accomplished a stereoselective synthesis of the diene system by (i) trapping a π‐allyl palladium complex with lithium diphenylphosphinite to give an allylic diphenylphosphane oxide and (ii) a subsequent Horner−Wittig reaction. The species that brings about the oxidative 1,4‐addition is benzeneperoxyseleninic acid. We also report observations that shed some light on the mechanism. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) |
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| AbstractList | Oxidation of 4,6-heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5-(3-hydroxypropenyl)dihydrofuran-2-one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six-membered ring as part of the s-traps-diene system was an intermediate in a strigol total synthesis; a second system lacking the six-membered ring is the subject of the present publication. We accomplished a stereoselective synthesis of the diene system by (i) trapping a pi-allyl palladium complex with lithium diphenylphosphinite to give an allylic diphenylphosphane oxide and (ii) a subsequent Horner-Wittig reaction. The species that brings about the oxidative 1,4-addition is benzeneperoxyseleninic acid. We also report observations that shed some light on the mechanism. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002). Oxidation of 4,6‐heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5‐(3‐hydroxypropenyl)dihydrofuran‐2‐one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six‐membered ring as part of the s‐trans‐diene system was an intermediate in a strigol total synthesis; a second system lacking the six‐membered ring is the subject of the present publication. We accomplished a stereoselective synthesis of the diene system by (i) trapping a π‐allyl palladium complex with lithium diphenylphosphinite to give an allylic diphenylphosphane oxide and (ii) a subsequent Horner−Wittig reaction. The species that brings about the oxidative 1,4‐addition is benzeneperoxyseleninic acid. We also report observations that shed some light on the mechanism. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) Oxidation of 4,6‐heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5‐(3‐hydroxypropenyl)dihydrofuran‐2‐one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six‐membered ring as part of the s ‐ trans ‐diene system was an intermediate in a strigol total synthesis; a second system lacking the six‐membered ring is the subject of the present publication. We accomplished a stereoselective synthesis of the diene system by (i) trapping a π‐allyl palladium complex with lithium diphenylphosphinite to give an allylic diphenylphosphane oxide and (ii) a subsequent Horner−Wittig reaction. The species that brings about the oxidative 1,4‐addition is benzeneperoxyseleninic acid. We also report observations that shed some light on the mechanism. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) |
| Author | Findeisen, Matthias Hennig, Lothar Reinhard, Gerd Oehme, Ramona Buff (née Kranz), Angelika Schulz (née Samson), Emmanuelle Galkina, Anna Welzel, Peter |
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| Keywords | STEREOISOMERS PALLADIUM-CATALYZED SUBSTITUTION HORNER-WITTIG REACTION oxidation FORMAL TOTAL-SYNTHESIS REARRANGEMENT ALLYLIC ALCOHOLS stereochemistry palladium SYSTEMS GERMINATION STIMULANT (+)-STRIGOL PHOSPHINE OXIDES olefination |
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| Snippet | Oxidation of 4,6‐heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to... Oxidation of 4,6-heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to... |
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| SubjectTerms | Chemistry Chemistry, Organic Olefination Oxidation Palladium Physical Sciences Science & Technology Stereochemistry |
| Title | Studies on an Oxidative 1,4-Addition to s-trans-1,3-Dienes, a Key Reaction in a Strigol Total Synthesis |
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