A novel synthesis of homologated allylic alcohols using dimethylsulphonium methylide

Harnett, J. J.; Alcaraz, Lilian; Mioskowski, Charles; Martel, Jean-Philippe; Gall, Thierry Le; Shin, Dong Soo; Falck, John R.

doi:10.1016/s0040-4039(00)73035-8

Cited by 20 publications

(2 citation statements)

References 6 publications

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“…Useful reagents that have been developed for the synthesis of allyl alcohols include the following: (ix) 1-chloroalkyl phenyl sulfoxide via α,β-epoxyalkyl sulfoxides; (x) dimethylsulfonium methylide; (xi) α-lithio selenoxides, (xii) α-(diphenylphosphinoyl)acetaldehydes by the intermolecular pinacol cross-coupling with saturated aldehydes; (xiii) β-acyloxy sulfones …”

Section: Introductionmentioning

confidence: 99%

Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl Alcohols

1998

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Reactions of α-aryl-, α-heteroaryl-, and α-heteroatom-substituted masked alkenyllithiums with aldehydes and ketones provide a general method for the synthesis of allylic alcohols substituted with an aryl or heteroaryl in the β position and aryl, heteroaryl or alkyl substituents in the α position via a [1,4]-C→O silicon rearrangement. In the case of reactions with enolizable aldehydes and ketones, anhydrous CeCl3 was used as an additive. High diastereoselectivities are observed for allyl alcohols produced from α-substituted aldehydes.

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Section: Introductionmentioning

confidence: 99%

Efficient Syntheses of Secondary and Tertiary 2-Aryl- and 2-Heteroaryl-allyl Alcohols

1998

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“…The well-established accessibility and versatility of epoxides have made them one of the key intermediates of modern organic synthesis . Since Corey and Chaykovsky's report in 1965, dimethylsulfonium methylide 1 has been the reagent of choice for the conversion of ketones and aldehydes to terminal epoxides. , More recently, Mioskowski et al reported some useful and novel applications of 1 for the direct conversion of ketones to allylic alcohols, the conversion of halides and mesylates to one-carbon homologated terminal alkenes, and finally the conversion of epoxides to the corresponding homologated allylic alcohols. , In the latter case, transformation was originally thought to be limited to terminal or activated (allylic/benzylic) epoxides. However, the potential synthetic interest of compounds which would result from the opening of unactivated epoxides prompted us to reinvestigate the reaction.…”

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confidence: 99%