Use of cyclopropanes and their derivatives in organic synthesis

Wong, H. N. C.; Hon, Moon Yuen; Tse, Chun Wah; Yip, Yu Chi; Tanko, James M.; Hudlický, Tomáš

doi:10.1021/cr00091a005

Cited by 939 publications

(324 citation statements)

References 97 publications

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“…Taking advantage of the reactivity of polarized donor-acceptor (D-A) cyclopropanes (40) [51,52] due to ring strain [53] and their behavior as carbocation upon Lewis acid activation, the Read de Alaniz group found an alternative method to trigger the rearrangement and obtain highly functionalized cyclopent-2-enones (41) (Scheme 18, A). The protocol obviated the problems that Piancatelli and D'Auria [15] encountered when they tried to prepare cyclopent-2-enones with a quaternary carbon through the Piancatelli rearrangement starting from a furan with a tertiary carbinol side chain (42) and a large amount of dehydrated compound was found together with the rearranged product (Scheme 18, B).…”

Section: Intermolecular Aza-piancatelli Rearrangementmentioning

confidence: 99%

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

2013

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Nearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many natural products. The main features of this reaction are the simple experimental conditions, the stereochemical outcome and the generality of the procedure. Consequently, a re-emergence of this reaction has been seen recently, including developments of the Piancatelli rearrangement with some interesting inter-and intramolecular variants. This review will mainly focus on the general aspects of the reaction along with its more recent applications.

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Section: Intermolecular Aza-piancatelli Rearrangementmentioning

confidence: 99%

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

2013

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“…They are often present as structural sub-units in natural and non-natural products (Rappoport, 1987;Burke and Grieco, 1979;Hudlicky et al, 1985;Ho, 1988;Burgess and Ho, 1994), are frequently used as mechanistic probes to elucidate reaction pathways (Suckling, 1988;Silverman et al, 1993;Newcomb and Chestney, 1994;Caldwell and Zhou, 1994;Husbands et al, 1994), and are increasingly valuable as synthetic intermediates (Wong et al, 1989;Davies, 1991;Reissig, 1995).…”

Section: Cyclopropanes and Cyclopropenesmentioning

confidence: 99%

Dirhodium(II) Carbenes : The Chiral Product Cascade

Roos

Raab

Al-Hatmi

2000

SQU Journal for Science

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ABSTRACT:The last decade has witnessed enormous growth in the spectrum of highly efficient asymmetric synthetic transformations. One prominent example of this progress is the application of dirhodium (II) carbenes generated from diazoprecursors. Innovative construction of 'designer' catalysts has played a integral role in extending the breadth of the synthetic cascade of non-racemic products now available through the range of cyclopropanation, C-X insertion, aromatic cycloaddition-rearrangement, and ylide-based reaction types. This review deals briefly with an overview of the important catalytic systems and maintains as its primary focus the cascade of diverse optically enriched products that flow from their applications. ROOS, RAAB, and AL-HATMI 74 CONTENTS

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“…1 Either the cyclopropyl or the cyclobutyl is a relatively highly reactive group and are frequently used as an intermediate in organic synthesis. 2,3 Compounds containing the cyclopropylpyridine moiety exhibit antibiotic, 4 antidepressant and anticancer activity. 5 The cyclopropylpyridines can be prepared by reaction of the appropriate vinylpyridine with diazocompounds 6,7 or dimethylsulfoniummethylide,about the C-C bond connecting the cyclo(propyl and butyl) and pyridinium groups (α) has been calculated at 30 o interval with full geometric optimization at the each point.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-cyclo(propyl- and butyl)-1-ethylpyridinium bromides and calculation of their proton and carbon chemical shifts

Eicher‐Lorka¹,

Kuodis²,

Matijoška³

et al. 2010

Arkivoc

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New 4-cyclo(propyl-and butyl)pyridinium salts have been prepared by alkylation of 4-picolinium salt with α,ω-dibromoalkanes under phase-transfer catalysis conditions. The influence of the nature and the catalysis concentration was investigated. The experimentally determined H and C NMR chemical shifts were compared with the values calculated using the GIAO/DFT and HF approach in gas-phase and/or in methanol by using the IEF-PCM method.

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Use of cyclopropanes and their derivatives in organic synthesis

Cited by 939 publications

References 97 publications

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

Dirhodium(II) Carbenes : The Chiral Product Cascade

Synthesis of 4-cyclo(propyl- and butyl)-1-ethylpyridinium bromides and calculation of their proton and carbon chemical shifts

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