Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes

Fürstner, Alois; Kollegger, Gerlinde M.; Weidmann, Hans

doi:10.1016/0022-328x(91)86327-m

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Cited by 42 publications

(29 citation statements)

References 17 publications

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“…Even Reformatsky reactions are known, although subsequent Brook rearrangement and elimination of trialkylsilanolate, to give alkenes, was observed in some cases (Scheme 64)164 .…”

mentioning

confidence: 99%

Acyl Silanes

Page¹,

McKenzie²,

Klair³

et al. 2009

Patai's Chemistry of Functional Groups

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“…Even Reformatsky reactions are known, although subsequent Brook rearrangement and elimination of trialkylsilanolate, to give alkenes, was observed in some cases (Scheme 64)164 .…”

mentioning

confidence: 99%

Acyl Silanes

Page¹,

McKenzie²,

Klair³

et al. 2009

Patai's Chemistry of Functional Groups

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“…Treating a 2,3-cyclic acetal derivative with 1 gives the free allylic alcohol-substituted glycal by acetal ring fragmentation. [17][18][19]22,24 Reaction of 2,3:4,6-di-O-isopropylidenemannopyranosyl bromide 56 with 1 gave 4,6-O-isopropylidene glucal 9 (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Rapid Preparation of Variously Protected Glycals Using Titanium(III)

1999

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Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp 2 Ti[III]Cl) 2 . This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid-and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. β-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

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“…[5] Palladium Catalyzed Cross-coupling Reaction of (2E,4Z )-5-Bromopenta-2,4-dienal 2 [5] Palladium Catalyzed Cross-coupling Reaction of (2E,4Z )-5-Bromopenta-2,4-dienal 2…”

Section: Methodsmentioning

confidence: 99%

Palladium Catalyzed Cross-Coupling Reaction of Functional Organozinc Reagents with (2E,4E)- and (2E,4Z)-5-Bromopenta-2,4-dienals: Easy Access to Functional Conjugated Dienic Aldehydes

Vicart

Saboukoulou

Ramondenc

et al. 2003

Synthetic Communications

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Functional zinc reagents can be applied to palladium catalyzed crosscoupling reaction with (2E,4E )-and (2E,4Z )-5-bromopenta-2,4dienal. The corresponding functional dienic aldehydes were obtained in goods yields. From the (2E,4E ) isomer, the (2E,4E ) dienals were isolated as single isomer according to a total stereoselective reaction. But, from the (2E,4Z ) isomer the coupling reaction has lead to a mixture of (2E,4E ) and (2E,4Z ) isomers. A mechanism for the loss of stereoselectivity in the last case is proposed.

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Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes

Cited by 42 publications

References 17 publications

Acyl Silanes

Acyl Silanes

Rapid Preparation of Variously Protected Glycals Using Titanium(III)

Palladium Catalyzed Cross-Coupling Reaction of Functional Organozinc Reagents with (2E,4E)- and (2E,4Z)-5-Bromopenta-2,4-dienals: Easy Access to Functional Conjugated Dienic Aldehydes

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