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Stereocontrolled La...
Stereocontrolled Lactonization Reactions via Palladium-Catalyzed 1,4-Addittion to Conjugated Dienes
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- Bäckvall, Jan-E. (författare)
- Uppsala universitet,Organisk kemi I
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Granberg, Kennth L. (författare)
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- Andersson, Pher (författare)
- Uppsala universitet,Organisk kemi I
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Gatti, Roberto (författare)
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- Gogoll, Adolf (författare)
- Uppsala universitet,Organisk kemi I
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(creator_code:org_t)
- 2002-05-01
- 1993
- Engelska.
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 58:20, s. 5445-5451
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Stereocontrolledp alladium(I1)-catalyzed1 ,4-chloro-and 1,4-acetoxylactonizations o f conjugated cyclic dienes have been developed to give stereodefined fused lactones. The stereochemistry of the 1,4- acetoxylactonization was controlled by the ligand on the metal catalyst, and in this way either a cisor truns-acetoxylactonization was obtained. This dual stereoselectivity is explained by a stereocontrolled acetate attack (trans or cis, respectively) on the allyl group in the catalytic (π-allyl)- palladium intermediate. To further strengthen the mechanism the intermediate (π-ally1)palladium complex was isolated and fully characterized. A stereospecific synthesis of cis- and truns-2-[6- (benzyloxy)-2,4-heptadien-l-yllacetic a cid (cis- and truns-9) followed by stereoselective Pd(I1)- catalyzed chloro- and acetoxylactonization in acetonelacetic acid resulted in highly functionalized fused lactones with control of the relative stereochemistry at four different carbons.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- Organic chemistry
- Organisk kemi
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- ref (ämneskategori)
- art (ämneskategori)
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