Iodoenolcyclisation of 2-(1,3-disubstituted-1-allyl)-1,3-dicarbonyl compounds: diastereoselective synthesis of tetrasubstituted dihydrofurans |
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| Authors: | Roberto Antonioletti Savina MalanconaFabrizio Cattaruzza Paolo Bovicelli |
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| Affiliation: | C.N.R. Istituto di Chimica Biomolecolare—Sezione di Roma, c/o Dipartimento di Chimica, Università di Roma “La Sapienza”, p.le A. Moro 5, Box 34 Roma 62, I-00185 Rome, Italy |
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| Abstract: | The I2-induced cyclisation of 2-alkenyl-1,3-dicarbonyl compounds with the mono- and di-substituted double bond occurred with good diastereoselectivity. A study of stereochemical aspects for different substituents on the allyl side chain was carried out. When the substituents were alkyl groups, the trans isomers formed preferentially, in the case of aromatic substituents the reaction lead instead to cis isomers. |
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| Keywords: | iodocyclization 1,3-dicarbonyl compounds 2,3-dihydrofurans furans |
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