Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction

Date

2011-06-15

Author

ÇAYİR, Merve
Demirci, Sema
Sezer, Serdar
Tanyeli, Cihangir

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A ring closing metathesis reaction of dienes and a ring closing enyne metathesis reaction derived from allyl, homoallyl and homopropargyl alcohol backbones are described. 2-Heteroaryl substituted allyl, homoallyl and homopropargyl alcohols have been easily and efficiently resolved through enzymatic resolution with high ee (93-99%) and known stereochemistry. Enantiomerically enriched dienes derived from allyl and homoallyl alcohols afforded the corresponding enantiomerically enriched dihydrofuran and dihydropyran derivatives, respectively, with chemical yields which varied between 72% and 88%. On the other hand, enantiomerically enriched enynes derived from homoallyl and homopropargyl alcohols gave the corresponding optically active dihydropyrans with conjugated diene units with chemical yields between 70% and 80%. A subsequent Diels-Alder reaction of the dihydropyran derivatives with a diene unit with tetracyanoethylene resulted in the formation of a diastereomeric dihydroisochromene ring system as the sole product.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/46616

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2011.07.003

Collections

Department of Chemistry, Article

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Citation Formats

M. ÇAYİR, S. Demirci, S. Sezer, and C. Tanyeli, “Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction,” TETRAHEDRON-ASYMMETRY, pp. 1161–1168, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/46616.