Rhodium-catalyzed highly diastereoselective intramolecular [4+2] cycloaddition of 1,3-disubstituted allene-1,3-dienes

RhCl(PPh3)(3)-catalyzed [4 + 2] intramolecular cycloaddition of allene-1,3-dienes afforded cis-fused [3.4.0]-bicyclic products with three chiral centers in good yields with excellent chemo- and diastereoselectivity. The configuration of the C?C bonds in the 1,3-diene unit controls the relative confi...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 18; pp. 2680 - 2684
Main Authors Han, Yulin, Ma, Shengming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.09.2018
Royal Society of Chemistry
Subjects
Allene
Catalysis
Chemistry
Chemistry, Organic
Configurations
Cycloaddition
Dienes
Organic chemistry
Physical Sciences
Rhodium
Science & Technology
Stereoselectivity
COMPLEX
DIENES
DIELS-ALDER REACTIONS
DIPHOSPHINES
1,3-DIENE
STEREOSELECTION
ALLENES
ALKYNES
CYCLOISOMERIZATION REACTIONS
CYCLIZATION
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Summary:RhCl(PPh3)(3)-catalyzed [4 + 2] intramolecular cycloaddition of allene-1,3-dienes afforded cis-fused [3.4.0]-bicyclic products with three chiral centers in good yields with excellent chemo- and diastereoselectivity. The configuration of the C?C bonds in the 1,3-diene unit controls the relative configurations of the non-bridging tertiary carbon atom in the six-membered ring. Based on the experimental results, a mechanism involving cyclometalation has been proposed.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c8qo00650d