Radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo-, and stereoselectivity

doi:10.1021/JO00037A026

Paper

Radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo-, and stereoselectivity

Published May 1, 1992 · M. Journet, M. Malacria

Journal of Organic Chemistry

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Abstract

Radical cyclization of (bromomethyl)-dimethylsilyl propargyl ether derivatives 1 is a powerful reaction with a high degree of regio-, chemo-, and stereoseletivity. Trisubstituted olefins 3, cyclopentene derivatives 5, and diquinane system 7j are obtained in good yields by a judicious choice of unsaturated substituents. Triquinane frameworks could be obtained stereoselectively from a suitable acyclic substrate of type 1 in a one-pot reaction. First attempts have not yet allowed us to aim at this goal due to interesting (1,5) hydrogen transfers.Moreover ,we have intercepted the α-cyclopropyl radical which is involved in the Stork-Beckwith mechanism of the 5-versus 6-membered ring formation in the vinyl radical cyclization

Study Snapshot

Radical cyclization of (bromomethyl)-dimethylsilyl propargyl ethers offers high regio-, chemo-, and stereoselectivity for the synthesis of trisubstituted olefins, cyclopentene derivatives,

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo-, and stereoselectivity

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References

Citations

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Direct construction of vicinal all-carbon quaternary stereocenters in natural product synthesis.

Recent efforts have successfully constructed vicinal all-carbon quaternary stereocenters in single-step operations, leading to the total synthesis of natural products with diverse biological and pharmacological activities.

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Manganese(III) acetate-mediated oxidative radical cyclizations enable the synthesis of densely functionalized cyclopentane-lactones with high stereocontrol and vicinal all-carbon quaternary stereocenters.

Enantioselective Cycloisomerization of 1,5‐Enynes Promoted by Cyclometalated NHC–PtII–Monophos Catalysts

Enantioselective cycloisomerization of 1,5-enynes using Monophos-PtII and Binepine-PtII complexes reveals a significant effect of the stereogenic carbon on the stereochemical outcome.