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Title: Highly regioselective diels-alder cycloaddition of 1,1-dimethyl-1,3-butadienes under lewis acid catalysis : application to taxoid synthesis
Authors: Dai, Wei-Min
Lau, Chi Wai
Keywords: Diels-Alder cycloaddition
Lewis acid catalysis
Issue Date: 1997
Citation: Proceedings of Symposium on Frontiers of Chemistry - in conjunction with the Second Conference for Worldwide Chinese Young Chemists (CWCYC-2), p. 145-146
Abstract: It has been known that substituents have a significant effect on the reactivity and selectivity of the Diels-Alder cycloaddition. Very recently, Roush and Barda reported the highly selective Diels-Alder cycloadditions of acyclic (Z)-1,3-dienes under Lewis acid catalysis. During past several years, we have been working on Lewis acid catalyzed Diels-Alder reactions of 2 with a series of dienophiles and observed some unusual reactivities arising from the steric interaction between the diene and the dienophiles. In this presentation, the reaction mechanisms are discussed based on our results obtained from experiments and computational calculations.
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