Reactions of diazoalkanes with unsaturated compounds

Джемилев, У. М.; Докичев, В. А.; Sultanov, S. Z.; Хуснутдинов, Р. И.; Tomilov, Yu. V.; Нефедов, О. М.; Толстиков, Г. А.

doi:10.1007/bf00956960

Cited by 11 publications

(12 citation statements)

References 6 publications

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“…These results are in line with the findings of Dzhemilev et al, who investigated the efficiency of a variety of transition metal catalysts in cyclopropanations of alkenes with diazomethane, and found that, for instance, norbornene did not react with CH 2 N 2 /Rh 2 (OAc) 4 , whereas Pd-based catalysts (Pd(OAc) 2 or Pd(acac) 2 ) were quite effective. [25] Moreover, two attempts to cyclopropanate endoperoxide 11 with ethyl diazocarboxylate (EDA) in the presence of catalytic amounts of Rh 2 (OAc) 4 failed, leading to an intractable mixture in which no peroxidic material was found.…”

mentioning

confidence: 99%

Palladium‐Catalyzed Cyclopropanation of Unsaturated Endoperoxides. A New Peroxide‐Preserving Reaction

Emerzian

Davenport²,

Song³

et al. 2009

Adv Synth Catal

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Unsaturated bicyclic endoperoxides are efficiently cyclopropanated with excess diazomethane in the presence of catalytic Pd(OAc)2 in a stereoselective manner. This method represents a new peroxide preserving transformation. Whereas the unsaturated endoperoxides in the [2.2.1] series are attacked by the carbene from the exo face, the analogs with larger bridges are preferentially attacked from the face syn to the peroxo bridge. Only in the case of the benzannelated [2.2.2] system the attack occurs exclusively from the face proximal to the benzene ring. Certain strained cyclopropanated endoperoxides are reduced by diazomethane to give cis-diols. 1-Methylfuran endoperoxide gives rise to cis-1-formyl-2-acetylcyclopropane in excellent yield.

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mentioning

confidence: 99%

Palladium‐Catalyzed Cyclopropanation of Unsaturated Endoperoxides. A New Peroxide‐Preserving Reaction

Emerzian

Davenport²,

Song³

et al. 2009

Adv Synth Catal

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“…9 Other general methods for the synthesis of the native hydrocarbon include the Wittig reaction of cyclopropanecarbaldehyde (6), 10 Bamford-Stevens reaction of cyclopropylethyl hydrazine derivative 7, 11 copper-zinc mediated elimination reaction of compound 8, 12 and palladium-catalyzed cyclopropanation of buta-1,3-diene with diazomethane (Scheme 1). 13…”

Section: Figure 1 Types Of Vinylcyclopropanesmentioning

confidence: 99%

Recent Advances in the Synthesis and Reactivity of Vinylcyclopropanes

2016

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In this review, we present the recent advances in the synthesis and reactivity of vinylcyclopropanes (VCPs). Various important methodologies involving ylides, carbenoid chemistry, metal-mediated cycloaddition reactions, and allylic cyclization methodologies for the synthesis of VCPs are described. Based on the type of VCPs, their reactivity is dealt under electrophile-, radical-, and nucleophile-mediated reactions. Several examples from transition-metal-mediated ring-opening reactions are discussed. 1 Introduction 2 Synthetic Routes to Vinylcyclopropanes 2.

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“…Cyclopropanation of methylenecyclobutane ( 9 ) with a solution of diazomethane 10 in diethyl ether in the presence of Pd(acac) 2 as a catalyst gave spiro[2.3]hexane ( 11 ) in 48% yield (Scheme ) …”

Section: Catalyzed Addition Of Diazo Compounds Leading To Spiransmentioning

confidence: 99%