1,2-Dihydropentalenes from Fulvenes by [6 + 2] Cycloadditions with 1-Isopropenylpyrrolidine

In situ generated acetone pyrrolidine enamine undergoes [6 + 2] cycloadditions with fulvenes to give 1,2-dihydropentalenes. This ring annulation method works particularly well with 6-monosubstituted fulvenes and is subject to steric hindrance at C-6 of the fulvene. On the basis of mechanistic studie...

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Published inOrganic letters Vol. 13; no. 22; pp. 5952 - 5955
Main Authors Coşkun, Necdet, Ma, Jingxiang, Azimi, Saeed, Gärtner, Christian, Erden, Ihsan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.11.2011
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Hydrogenation
Molecular Structure
Physical Sciences
Pyrrolidines - chemistry
Science & Technology
SUBSTITUTED FULVENES
CHEMISTRY
ACETONE
ROUTE
SINGLET OXYGEN
ALLENE OXIDE
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Summary:In situ generated acetone pyrrolidine enamine undergoes [6 + 2] cycloadditions with fulvenes to give 1,2-dihydropentalenes. This ring annulation method works particularly well with 6-monosubstituted fulvenes and is subject to steric hindrance at C-6 of the fulvene. On the basis of mechanistic studies, optimal conditions have been developed for a one-pot synthesis of 1,2-dihydropentalenes using catalytic amounts of pyrrolidine.
Bibliography:On leave from Uludag University, Department of Chemistry, 16059 Bursa, Turkey.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202222d