Lewis base effects in the Baylis-Hillman reaction of imines with cyclohex-2-en-1-one and cyclopent-2-en-1-one |
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Authors: | Shi M Xu Y M |
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Institution: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. mshi@pub.sioc.ac.cn |
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Abstract: | In the Baylis-Hillman reaction of N-benzylidene-4-methyl-benzenesulfonamide with cyclohex-2-en-1-one or cyclopent-2-en-1-one, we found that, in the presence of a catalytic amount of DMAP, the Baylis-Hillman reaction can be greatly accelerated to give the normal Baylis-Hillman adduct 1 or 3 in good or very high yields: moreover, using PBu3 as a Lewis base in the reaction of N-benzylidene-4-methylbenzenesulfonamide with cyclopent-2-en-1-one, the normal Baylis-Hillman adducts 3 could be obtained in very high yields within 5 h, however, using PBu3 or DBU as a Lewis base in the reaction of N-benzylidene-4-methyl-benzenesulfonamide with cyclohex-2-en-1-one, beside the normal Baylis-Hillman adduct 1 abnormal Baylis-Hillman adduct 3-aryl-2-(4-methylphenyl)sulfonyl]-2-azabicyclo2.2.2]octan-5-one 2 was formed at the same time; the substituent's effects were also examined. |
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