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Claisen rearrangement
About: Claisen rearrangement is a research topic. Over the lifetime, 3783 publications have been published within this topic receiving 57974 citations.
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TL;DR: In this paper, the titled Claisen modification is shown to proceed with a remarkably high level of diastereoselection and asymmetric transmission by virtue of the proper choice of the combination of the silyl triflate and the tertiary amine used.
Abstract: The titled Claisen modification is shown to proceed with a remarkably high level of diastereoselection and asymmetric transmission by virtue of the proper choice of the combination of the silyl triflate and the tertiary amine used.
TL;DR: In this article, a new synthesis of mycophenolic acid was achieved using silyloxy-1,3-cyclohexadiene, which undergoes cycloaddition to dimethyl acetylenedicarboxylate and subsequent elimination of ethylene (Alder-Rickert reaction) to give the trisubstituted dimethyl phthalate 11.
Abstract: A new synthesis of mycophenolic acid 1, has been accomplished using silyloxy-1,3-cyclohexadiene 9 which undergoes cycloaddition to dimethyl acetylenedicarboxylate and subsequent elimination of ethylene (Alder-Rickert reaction) to give the trisubstituted dimethyl phthalate 11. After conversion of 11 to phthalide 16, the (E)-4-methyl-4-hexenoic acid side-chain was constructed via an orthoester Claisen rearrangement using allylic alcohol 19 and triethyl orthoacetate.
TL;DR: Microwave assisted double decarboxylative Claisen rearrangement of bis(allyl) 2-tosylmalonates provides substituted 1,6-heptadienes, which may be alkylated, and then converted into pyridines by ozonolysis followed by reaction with ammonia generated in situ under microwave conditions.
Abstract: Microwave-assisted double decarboxylative Claisen rearrangement of bis(allyl) 2-tosylmalonates provides substituted 1,6-heptadienes, which may be alkylated, and then converted into pyridines by ozonolysis followed by reaction with ammonia generated in situ under microwave conditions.