Stereoselective synthesis of spirocyclic cyclopentapyrans by the Pauson-Khand reaction on camphor tethered enynes

Date

2008-12-01

Author

Sezer, Serdar
Gumrukcu, Yasemin
ŞAHİN, Ertan
Tanyeli, Cihangir

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An intramolecular Pauson-Khand reaction of camphor tethered enynes derived from homoallyl, homomethallyl and homopropargyl alcohols is described. Homoallyl, homomethallyl, and homopropargyl moieties are easily constructed on the camphor carbonyl group with excellent diastereoselectivity due to endo-face selectivity, and with known stereochemistry. Each enantiomerically pure enyne affords the conformationally most stable diastereomeric spirocyclic cyclopenta[c]pyran ring system.

Subject Keywords

Ring-closing metathesis, Auxiliaries, Alcohols, Complexes, Derivatives, Spiroketals, Formal synthesis, Asymmetric-synthesis, Conformational control, Remote stereochemistry

URI

https://hdl.handle.net/11511/43985

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2008.11.020

Collections

Department of Chemistry, Article

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Citation Formats

S. Sezer, Y. Gumrukcu, E. ŞAHİN, and C. Tanyeli, “Stereoselective synthesis of spirocyclic cyclopentapyrans by the Pauson-Khand reaction on camphor tethered enynes,” TETRAHEDRON-ASYMMETRY, pp. 2705–2710, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/43985.