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Regio- and Stereoselective Synthesis of Vinylallenes by 1,5-(SN′′)-Substitution of Enyne Acetates and Oxiranes with Organocuprates

✍ Scribed by Martin Purpura; Norbert Krause

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
210 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

Enyne acetates 2, 4, 6, and 8, as well as enyne oxiranes 10, isomers; however, pure (E)-vinylallenes are formed occasionally. The 1,5-substitutions can also be carried out with with different substitution patterns react with organocuprates regioselectively under 1,5-(S N 2ЈЈ)-substitution to catalytic amounts of copper reagents. The reaction of chiral enyne acetate (S)-2a with tBu 2 CuLi • LiCN proceeds provide vinylallenes 11 and 12. With lithium dimethylcuprate, reduced vinylallenes originating from a (formal) enantioselectively, so that this transformation constitutes a new case of remote stereocontrol. transfer of a hydride ion to the substrate are formed in some cases. The products are usually obtained as mixtures of (E/Z)-

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