A new route to seven-and eight-membered carbocycles

U, Jong Sun; Lee, Jinhwa; Kun, Jin

doi:10.1016/s0040-4039(97)01142-8

Cited by 33 publications

(1 citation statement)

References 17 publications

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“…In 1997, Cha and co-workers reported a stepwise protocol for the synthesis of six-to eight-membered ring carbocyclic conjugated enones via a sequential intramolecular Kulinkovich cyclopropanation followed by an FeCl 3 -mediated ring opening and NaOAc-mediated dehydrochlorination. 161 This reaction likely involves the β-chloro ketone intermediate 297 that is formed via trapping of the β-keto radical, ultimately resulting in α,β-unsaturated ketone 298 after elimination (Scheme 70).…”

Section: C−c Bond Cleavage To Generate β-Ketomentioning

confidence: 99%

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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The carbon–carbon (C–C) bond cleavage of cyclopropanols is a wide area of research with much current activity. This review highlights new developments in this area over the past two decades. A summary is made of the three main reactivity modes, namely, homoenolate chemistry, β-keto radical chemistry, and acid-catalyzed ring-opening, as well as all other methods for the C–C bond cleavage and functionalization of cyclopropanols, including base-mediated ring-opening, metal-catalyzed C–C insertions and eliminations, oxidative fragmentation using hypervalent iodine reagents, reactions of donor–acceptor cyclopropanols, and pericylic reactions. Emphasis is placed on the synthetic utility of cyclopropanols and related derivatives, which have emerged as unique three-carbon synthons.

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Section: C−c Bond Cleavage To Generate β-Ketomentioning

confidence: 99%

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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Enantio- und diastereoselektive Synthese von 2-substituierten 1-Bicyclo[3.1.0]hexanolen

Mizojiri¹,

Urabe²,

Sato³

1998

Angewandte Chemie

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Nützliche Zwischenstufen für die organische Synthese sind die optisch aktiven, substituierten bicyclischen Cyclopropanole, die mit gängigen Methoden nur schwer zugänglich sind. Sie können nun aus Oppolzer‐N‐Acylcamphersultamen und [Ti(OiPr)2(η2‐Propen)] mit hoher Enantio‐ und Diastereoselektivität einfach hergestellt werden [Gl. (a)]. R=Alkyl, Alkenyl, Benzyl, Alkoxyalkyl, Alkylsiloxyalkyl.

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The Kulinkovich Cyclopropanation of Carboxylic Acid Derivatives

Kun

Kulinkovich

2012

Organic Reactions

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Cyclopropanes are characterized by high ring‐strain energy and have been employed as useful building blocks in organic synthesis. The incorporation of a heteroatom donor substituent such as OH, OR, NR2, or SR on the ring imparts enhanced reactivity. Hydroxycyclopropanes (cyclopropanols) in particular have been thoroughly studied due to their facile ring cleavage. Among several known methods, a new method for preparation of cyclopropanols involves dialkoxytitanacyclopropane‐mediated cyclopropanation (the Kulinkovich cyclopropanation) of esters with Grignard reagent in the presence of titanium isopropoxide. The striking feature of this method is the facile formation of a three‐membered ring from a simple Grignard reagent which acts as a 1,2‐dicarbanion equivalent through a pivotal dialkoxytitana‐cycloproapne intermediate. These reactions benefit from the availability of inexpensive reagents, ease of operation, and high selectivity for cis ‐dialkylcyclopropanols. This cyclopropanation reaction has since been extended to other carboxylic derivatives to provide convenient access to several heteroatom‐substituted cyclopropanes. The objective of this chapter is to provide an updated, comprehensive coverage of the literature on the Kulinkovich cyclopropanation reaction and related processes. Key mechanistic issues are summarized.

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A new route to seven-and eight-membered carbocycles

Cited by 33 publications

References 17 publications

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

Enantio- und diastereoselektive Synthese von 2-substituierten 1-Bicyclo[3.1.0]hexanolen

The Kulinkovich Cyclopropanation of Carboxylic Acid Derivatives

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