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Synthesis of seven-membered carbocyclic rings via a microwave-assisted tandem oxyanionic 5-exo dig cyclization-claisen rearrangement process.

ABSTRACT: Appropriately substituted 1-alkenyl-4-pentyn-1-ol systems, readily prepared from simple starting materials, serve as useful precursors to a number of substituted cyclohept-4-enone derivatives via a microwave-assisted tandem oxyanionic 5-exo cyclization/Claisen rearrangement sequence. The reactions involving terminally substituted 4-pentyn-1-ols were found to be highly stereoselective, with the alpha and beta groups in the final product showing a strong preference for the trans orientation.

SUBMITTER: Li X

PROVIDER: S-EPMC2523263 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature

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Synthesis of seven-membered carbocyclic rings via a microwave-assisted tandem oxyanionic 5-exo dig cyclization-claisen rearrangement process.

Li Xin X Kyne Robert E RE Ovaska Timo V TV

The Journal of organic chemistry 20070727 17

Appropriately substituted 1-alkenyl-4-pentyn-1-ol systems, readily prepared from simple starting materials, serve as useful precursors to a number of substituted cyclohept-4-enone derivatives via a microwave-assisted tandem oxyanionic 5-exo cyclization/Claisen rearrangement sequence. The reactions involving terminally substituted 4-pentyn-1-ols were found to be highly stereoselective, with the alpha and beta groups in the final product showing a strong preference for the trans orientation. ...[more]

PMID: 17655366

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