Synthesis of Butenolides via Transition Metal2 Catalyzed Cyclization Reaction of 2 ,32Allenoic Acids

doi:10.7523/j.issn.2095-6134.2005.1.018

Abstract

Abstract:

Butenolides are a class of compounds of current interest due to their occurrence in natural products and the potential broad range of biological activities of natural and unnatural products. During the course of our study on transition metal-catalyzed cyclization reaction of 2 ,3-allenoic acids , we have developed palladium (Ⅱ)-catalyzed reaction of 2 , 3-allenoic acids with (ω-1 )-alkenyl halides to introduce sp32hybridized carbon atoms at the βposition of butenolides. In this reaction , we observed a new Pd (Ⅱ)2catalytic cycle which combines carbopalladation with repeated dehydropalladationP hydropalladation-β-dehalopalladation. Furthermore , a new area of oxidative cyclization-dimerization reaction of two functionalized allenes has been established. In this area , we have developed oxidative dimeric cyclization reaction of 2 , 3-allenoic acids to afford bi-butenolides. Moreover , oxidative cyclization-dimerization reaction of 2 ,3-allenoic acids with 1 ,2-allenyl ketones was also established to furnish interesting compounds with two different cycles in a single step.

Key words: butenolides, 2, 3-allenoic acids, palladium, cyclization, oxidative

CLC Number:

O627

Ma Shengming, Yu Zhanqian. Synthesis of Butenolides via Transition Metal2 Catalyzed Cyclization Reaction of 2 ,32Allenoic Acids[J]. , 2005, 22(1): 110-121.

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