DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene.

doi:10.1021/ja8099008

Paper

DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene.

Published Feb 26, 2009 · W. Zhang, Hua-Dong Xu, Hui Xu

Journal of the American Chemical Society

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Abstract

A DABCO-catalyzed highly regio- and stereoselective syn-1,4-bromolactonization of conjugated enynes was discovered. The 1,4-addition occurred selectively over 1,2-addition for most enynes. In contrast to anti 1,2-addition to alkenes, where two adjacent stereogenic centers are created, 1,4-addition across conjugated enynes can produce a stereogenic center and an axially chiral allene simultaneously. Enynes with Z and E configurations yielded products with complementary stereochemistries at the newly generated stereogenic center and axially chiral allene. Di-, tri-, or even tetrasubstituted allenes together with lactones can be efficiently and selectively prepared from this enyne bromolactonization reaction.

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Study Snapshot

DABCO-catalyzed 1,4-bromolactonization of conjugated enynes produces highly stereoselective products with complementary stereochemistries, enabling efficient and selective preparation of di-, tri-, or tetrasubstituted allenes and lactones.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene.

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