Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols

Bickley, Jamie F.; Gillmore, Adam T.; Roberts, Stanley M.; Skidmore, John; Steiner, Alexander

doi:10.1039/b008275i

Cited by 13 publications

(3 citation statements)

References 11 publications

(8 reference statements)

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“…After asymmetric epoxidation, the subsequent steps in the syntheses of 51, 52, and 54 are nucleophilic opening of the epoxide ring and Baeyer-Villiger oxidation of the ketones to the corresponding esters [85]. Tertiary epoxy alcohols such as 61 can be obtained with excellent diastereoselectivity by addition of Grignard reagents to epoxy ketones [88,89]. Similarly, intramolecular epoxide opening provides access to, e.g., enantiomerically pure flavonoids [86,87].…”

Section: Epoxidation Of Enones and Enoatesmentioning

confidence: 99%

Oxidation

2005

Asymmetric Organocatalysis

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Section: Epoxidation Of Enones and Enoatesmentioning

confidence: 99%

Oxidation

2005

Asymmetric Organocatalysis

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“…The final wR(F 2 ) was 0.0661(all data). Absolute configuration was not determined, Flack parameter 23 = 1.5 (19).…”

Section: Experimental Representative Experimental Procedure: (2s3s )-...mentioning

confidence: 99%

“…The stereochemistry of the products was assigned by comparison with a previously reported example in which the configuration was determined by X-ray crystallography. 19 Using epoxyalcohol 9, three readily available metal triflates, Sc(OTf ) 3 , La(OTf ) 3 and Yb(OTf ) 3 , were tested as rearrangement catalysts employing dichloromethane and acetonitrile as solvents. Initial reactions were performed using 20 mol% of the triflate catalysts.…”

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confidence: 99%

The semi-pinacol rearrangement of homochiral epoxyalcohols catalysed by rare earth triflates

Bickley

Hauer²,

Pena

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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Asymmetric Epoxidation of Electron‐Deficient Alkenes

Porter

Skidmore

2009

Organic Reactions

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Asymmetric epoxidation reactions have the distinction of being among the first enantioselective transformations to be widely sued in organic synthesis. The Sharpless asymmetric epoxidation is arguably one of the most important methods for the synthesis of enantiomerically enriched intermediates uses en route to a wide range of synthetic targets. To date most examples have employed electrophilic oxidizing agents and are thus applicable to electron‐neutral or electron‐rich double bonds. On the other hand alkenes substituted with electron‐withdrawing groups often react inefficiently with electrophilic oxidizing agents; such alkanes are more readily epoxidized using nucleophilic oxidants. The Weitz‐Scheffer epoxidation of alpha,beta‐unsaturated ketones to the corresponding epoxy ketones using basic hydrogen peroxide is the classical nucleophilic epoxidation reaction. This chapter considers the more general case of the conversion of an electron deficient alkene into the corresponding epoxide in an enantioselective fashion. Only methods based on chiral reagents or catalysts are covered. This review covers the literature to the end of 2005.

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Synthesis and reactions of some optically active epoxides formally derived from tertiary allylic alcohols

Cited by 13 publications

References 11 publications

Oxidation

Oxidation

The semi-pinacol rearrangement of homochiral epoxyalcohols catalysed by rare earth triflates

Asymmetric Epoxidation of Electron‐Deficient Alkenes

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