Chelation control in the [3+3] annulation reaction of alkoxy-substituted 1,1-diacylcyclopropanes with 1,3-bis(trimethylsilyloxy)-1,3-butadienes

Hefner, Jennifer; Langer, Peter

doi:10.1016/j.tetlet.2008.05.066

Cited by 7 publications

(2 citation statements)

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“…The cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 1-acetyl-1-formylcyclopropane and with 1-acetyl-1-benzoylcyclopropane proceeded by regioselective attack of the terminal carbon atom of the diene onto the more reactive carbonyl group (i.e., the formyl and the acetyl group, respectively). Recently, we have reported preliminary results related to the regiodirecting effect of chelating , alkoxy groups present in 1,1-diacylcyclopropane . Herein, we report full details and a comprehensive study of the scope of our methodology.…”

Section: Introductionmentioning

confidence: 99%

Chelation Control in the [3 + 3] Annulation Reaction of Alkoxy-Substituted 1,1-Diacylcyclopropanes with 1,3-Bis(trimethylsilyloxy)-1,3-butadienes. Diversity-Oriented Synthesis of Isochromanes

et al. 2010

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Functionalized arenes were prepared by chelation-controlled [3 + 3] cyclization/cyclopropane opening reactions of 1-trimethylsilyloxy-1,3-butadienes with benzyloxy- or methoxy-substituted 1,1-diacylcyclopropanes. A number of benzyloxy-substituted derivatives were transformed into isochromanes by deprotection and subsequent cyclization. Mixed chromanes-isochromanes were prepared starting with 1,3-bis(silyloxy)-1,3-butadienes containing a remote chloride group.

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Section: Introductionmentioning

confidence: 99%

Chelation Control in the [3 + 3] Annulation Reaction of Alkoxy-Substituted 1,1-Diacylcyclopropanes with 1,3-Bis(trimethylsilyloxy)-1,3-butadienes. Diversity-Oriented Synthesis of Isochromanes

et al. 2010

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“…The cyclization of diene 2a with 1,1-diacylcyclopropane 3f , containing a methoxy group, regioselectively afforded salicylate 6a (Scheme 6 ). 27 The formation of the product can be explained by chelation of the Lewis acid by the methoxy and the neighbouring carbonyl group, which is, thus, selectively activated and attacked by the diene to give intermediate A . Subsequent cyclization by attack of the central carbon atom of the diene to the second carbonyl group results in formation of the product.…”

Section: Reactions With Masked Dianionsmentioning

confidence: 99%

Adventures in the Chemistry of 1,1-Diacylcyclopropanes

Langer

2023

Synlett

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The present personalized account aims to highlight 1,1-diacylcyclopropanes as synthetic building blocks or target molecules. The chemistry presented includes cyclization reactions of 1,1-diacylcyclopropanes with free and masked dianions to give spirocyclopropanes as products or reactive intermediates that readily undergo ring-cleavage reactions. In addition, the synthesis of cyclopropylated 1,3,5-tricarbonyl compounds, containing two 1,1-diacylcyclopropane moieties, is discussed. Based on this work also other syntheses of cyclopropanes were developed.1 Introduction2 Reactions of Masked Dianions3 Reactions of Free Dianions4 Cyclopropylated 1,3,5-Tricarbonyl Compounds5 Miscellaneous6 Conclusions

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The Asymmetric Vinylogous Mukaiyama Aldol Reaction

Cordes

Kalesse

2019

Organic Reactions

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The vinylogous Mukaiyama aldol (VMA) reaction allows efficient access to larger segments for complex natural product synthesis, primarily polyketides, through the construction of vicinal hydroxyl and methyl groups as well as di‐ and tri‐substituted double bonds in a single operation. In this chapter, the current scope and limitations of this transformation, as well as its application in natural product synthesis, are discussed.

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Chelation control in the [3+3] annulation reaction of alkoxy-substituted 1,1-diacylcyclopropanes with 1,3-bis(trimethylsilyloxy)-1,3-butadienes

Cited by 7 publications

References 10 publications

Chelation Control in the [3 + 3] Annulation Reaction of Alkoxy-Substituted 1,1-Diacylcyclopropanes with 1,3-Bis(trimethylsilyloxy)-1,3-butadienes. Diversity-Oriented Synthesis of Isochromanes

Chelation Control in the [3 + 3] Annulation Reaction of Alkoxy-Substituted 1,1-Diacylcyclopropanes with 1,3-Bis(trimethylsilyloxy)-1,3-butadienes. Diversity-Oriented Synthesis of Isochromanes

Adventures in the Chemistry of 1,1-Diacylcyclopropanes

The Asymmetric Vinylogous Mukaiyama Aldol Reaction

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