Insertion of metallated epoxynitriles into organozirconocene chlorides. A convergent synthesis of 2-cyano-1,3-dienes

Kasatkin, Alexander N.; Whitby, Richard J.

doi:10.1016/s0040-4039(00)01006-6

Cited by 28 publications

(9 citation statements)

References 9 publications

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“…Lithiooxiranes stabilized by a carbethoxy 311 or a cyano 290,311,318 group can be readily prepared by deprotonation by LDA at −80 • C and quenched with various electrophiles. The lithiooxirane 193 (Scheme 85) is configurationally stable at this temperature, whereas α-cyano lithiooxiranes show 318 a limited configurational stability.…”

Section: Carbalkoxy-stabilized Lithiooxiranes and Related Compoundsmentioning

confidence: 99%

Reactivity of Oxiranes with Organolithium Reagents

Chemla

Vrancken

2009

Patai's Chemistry of Functional Groups

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Section: Carbalkoxy-stabilized Lithiooxiranes and Related Compoundsmentioning

confidence: 99%

Reactivity of Oxiranes with Organolithium Reagents

Chemla

Vrancken

2009

Patai's Chemistry of Functional Groups

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“…Whitby and Kasatkin have also described the addition of nitrile-stabilised a-lithiated epoxides to an alkenylzirconocene 110 (obtained by hydrozirconation of 1-octyne). 62 This chemistry allowed the convergent synthesis of a range of 2-cyano-1,3-dienes 112 (Scheme 40). Following on from the extensive studies of phenylsulfonyl-stabilised lithiated epoxides by Jackson et al, [63][64][65][66][67][68][69] Mori has reported the ability of these stabilised anions to be trapped with substituted alkyl iodides and triflates, as well as epoxides (Scheme 41).…”

Section: Scheme 39mentioning

confidence: 99%

Recent Developments in the Chemistry of Lithiated Epoxides

Hodgson¹,

Gras²

2002

Synthesis

102

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Although the lithium base-induced b-elimination of epoxides to allylic alcohols is a well-known reaction, a-lithiation has also been described many times. The resulting lithiated epoxides, first postulated as intermediates by Cope in 1951, have been invoked in a wide range of reactions, with their carbenoid properties allowing for very different reactivities. This review covers the recent advances (~1996-mid 2002) in the rich chemistry of these main-group metal carbenoids, especially their generation by enantioselective a-deprotonation.

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“…Alkenylzirconium compound 378 reacts with lithiated epoxy nitriles 379 to yield nitriles 380. 355 If pure epoxy nitrile isomers are used, the reaction still gives a mixture of geometric isomers at the cyano-substituted double bond.…”

Section: Sir3mentioning

confidence: 99%

Synthetic methodologies for carbo-substituted conjugated dienes

Васильев¹,

Serebryakov²

2001

Russ. Chem. Rev.

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We report the observation of changes in the wave turbulence properties of gravitycapillary surface waves due to a finite-depth effect. When the fluid depth is decreased, a hump is observed on the wave spectrum in the capillary regime at a scale that depends on the depth. The possible origin of this hump is discussed. In the gravity regime, the wave spectrum still shows a power law but with an exponent that strongly depends on the depth. A change in the scaling of the gravity spectrum with the mean injected power is also reported. Finally, the probability density function of the wave amplitude rescaled by its rms value is found to be independent of the fluid depth and to be well described by a Tayfun distribution.

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Insertion of metallated epoxynitriles into organozirconocene chlorides. A convergent synthesis of 2-cyano-1,3-dienes

Cited by 28 publications

References 9 publications

Reactivity of Oxiranes with Organolithium Reagents

Reactivity of Oxiranes with Organolithium Reagents

Recent Developments in the Chemistry of Lithiated Epoxides

Synthetic methodologies for carbo-substituted conjugated dienes

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