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Synlett 1996; 1996(8): 752-754
DOI: 10.1055/s-1996-5506
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BF3⋅Et2O-Mediated Intramolecular Allylstannane-Ketone Cyclizations: Formation of Bicyclo[4.1.0]hept-4-en-1-ols from 5-(Tributylstannyl)-3-cycloheptenones

Kei Takeda* , Akemi Nakajima, Eiichi Yoshii
  • *Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-01, Japan, Internet takedak@ms.toyama-mpu.ac.jp
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Publication Date:
31 December 2000 (online)

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In the reaction of trans- and cis-6-alkyl-5-(tributylstannyl)-3-(tert-butyldimethylsiloxy)-3-cycloheptenones with BF3⋅Et2O, the trans isomer afforded bicyclo[4.1.0]heptenol, intramolecular addition product of the allylstannane system to the carbonyl group, as the major product, while with the cis isomer predominant course was desilylation with retention of the SnBu3 group.

allylstannane - bicyclo[4.1.0]hept-4-en-1-ol - BF3⋅Et2O - cyclopropanol formation - [3+4] annulation

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