ChemInform Abstract: REGIOSELECTIVITY OF THE REACTIONS OF TRIALKYLALUMINUM REAGENTS WITH 2,3‐EPOXY ALCOHOLS: APPLICATION TO THE SYNTHESIS OF α‐CHIRAL ALDEHYDES

ROUSH, W. R.; Adam, Michael A.; Peseckis, Steven M.

doi:10.1002/chin.198329230

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“…Whereas reaction of epoxy alcohols with cuprates leads to epoxide opening at C2, reaction with trimethylaluminum generally leads to methylation of C3, and consequently, affords a 1,2-diol as the major product. [ 66 , 67 ] Banwell et al [ 68 ] exploited this transformation with the unsaturated epoxide ( R )-19 to prepare the tetrahydropyranylic core 143 of the phytotoxic polyketide herboxidiene ( Scheme 26 ). Thus, treatment of ( R )-19 with trimethylaluminum provided smooth conversion (opening occurred exclusively on C3) into a diol that was acetylated under standard conditions to obtain 141 .…”

Section: Epoxide Ring-opening At C3mentioning

confidence: 99%

Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation

Riéra

Moreno

2010

Molecules

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An overview of the synthesis and applications of chiral 2,3-epoxy alcohols containing unsaturated chains is presented. One of the fundamental synthetic routes to these compounds is Sharpless asymmetric epoxidation, which is reliable, highly chemoselective and enables easy prediction of the product enantioselectivity. Thus, unsaturated epoxy alcohols are readily obtained by selective oxidation of the allylic double bond in the presence of other carbon-carbon double or triple bonds. The wide availability of epoxy alcohols with unsaturated chains, the versatility of the epoxy alcohol functionality (e.g. regio- and stereo-selective ring opening; oxidation; and reduction), and the arsenal of established alkene chemistries, make unsaturated epoxy alcohols powerful starting materials for the synthesis of complex targets such as biologically active molecules. The popularization of ring-closing metathesis has further increased their value, making them excellent precursors to cyclic compounds.

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Section: Epoxide Ring-opening At C3mentioning

confidence: 99%

Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation

Riéra

Moreno

2010

Molecules

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: REGIOSELECTIVITY OF THE REACTIONS OF TRIALKYLALUMINUM REAGENTS WITH 2,3‐EPOXY ALCOHOLS: APPLICATION TO THE SYNTHESIS OF α‐CHIRAL ALDEHYDES

Abstract: Das Epoxid (I) reagiert mit Dimethyllithiumcuprat oder mit Triethylaluminium zu den beiden Spaltprodukten (II) bzw. (III) in unterschiedlichen Anteilen.

Cited by 1 publication

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Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation

Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation

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