Highly Regioselective Copper-Catalyzed cis- and trans-1-Propenyl Grignard Cleavage of Hindered Epoxides. Application in Propionate Synthesis

Hindered protected and unprotected epoxy alcohols were regioselectively cleaved using copper-catalyzed cis- and trans-1-propenylmagnesium bromide. The reaction exhibited good yield and excellent regioselectivity in systems where organocuprates and organoalanes failed. The cis Grignard reagent displa...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-07, Vol.71 (15), p.5826-5829
Main Authors: Rodríguez, David, Mulero, Marlenne, Prieto, José A
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Alkynes - chemistry
Catalysis
Chemistry
Copper - chemistry
Epoxy Compounds - chemistry
Epoxy Compounds - metabolism
Exact sciences and technology
Molecular Structure
Organic chemistry
Propionates - chemical synthesis
Propionates - chemistry
Stereoisomerism
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Summary:Hindered protected and unprotected epoxy alcohols were regioselectively cleaved using copper-catalyzed cis- and trans-1-propenylmagnesium bromide. The reaction exhibited good yield and excellent regioselectivity in systems where organocuprates and organoalanes failed. The cis Grignard reagent displayed no double-bond isomerization, whereas the trans isomer showed partial trans-to-cis equilibration, which was minimized by controlling the reagent formation conditions. The reaction was shown to be highly useful for the elaboration of the C10−C15 Streptovaricin D ansa chain fragment.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060833t