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Stereoselective access to substituted enediyne building blocks

โœ Scribed by George Hynd; Graham B. Jones; Gary W. Plourde II; Justin M. Wright

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
195 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Intermoleeular coupling-elimination of disubstituted propargyl bromides gives rise to diffe~-ntially substituted 3-hexen-l,5-diynes with E:Z selectivity an high as 100:1. Application of the methodology in the synthesis of key nanomaterial building blocks is demonstrated.

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An intramolecular Mannich reaction, involving various achiral aldehydes together with an a-chiral amine is employed as the key step for a stereocontrolled synthesis of highly substituted piperidine systems. Accordingly, 12 new piperidines bearing four asymmetric centers were prepared in six steps fr