Reaction of 4-methyl, 4-phenyl, and 4-hydrogen substituted 1-lithio-1,3-butadienes with aldehydes: preparation of multiply substituted cyclopentadienes |
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| Authors: | Zhihui Wang Zhenfeng Xi |
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| Institution: | a Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | Reaction of aldehydes with 1-lithio-1,3-butadiene reagents possessing a methyl substituent, a phenyl substituent or a hydrogen at position 4 of the butadienyl skeletons was studied. Polysubstituted cyclopentadiene derivatives were obtained in high yields upon hydrolysis using strong acidic solution. Reaction mechanism study revealed that these cyclopentadienes were formed via an acid-promoted cyclization of conjugated dienols. Thus, stereodefined all-cis substituted dienols or a wide diversity of substituted cyclopentadienes can be obtained from the same 1-lithio-1,3-butadiene reagent and aldehyde by adjusting the hydrolysis conditions. |
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