Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 40, 2009 - Issue 1

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Original Articles

Amberlyst-15–Catalyzed Efficient Cyclization of γ- and δ-Unsaturated Alcohols: Green Synthesis of Oxygen Heterocycles

Soni A. Singh Laboratory for Advanced Research in Natural and Synthetic Chemistry, V. G. Vaze College, University of Mumbai, Mumbai, India

Shilpi Kabiraj Laboratory for Advanced Research in Natural and Synthetic Chemistry, V. G. Vaze College, University of Mumbai, Mumbai, India

Reena P. Khandare Laboratory for Advanced Research in Natural and Synthetic Chemistry, V. G. Vaze College, University of Mumbai, Mumbai, India

Shrikant P. Nalawade Laboratory for Advanced Research in Natural and Synthetic Chemistry, V. G. Vaze College, University of Mumbai, Mumbai, India

Kiran B. Upar Laboratory for Advanced Research in Natural and Synthetic Chemistry, V. G. Vaze College, University of Mumbai, Mumbai, India

Sujata V. Bhat Laboratory for Advanced Research in Natural and Synthetic Chemistry, V. G. Vaze College, University of Mumbai, Mumbai, IndiaCorrespondence[email protected]

Abstract

Amberlyst-15 (H⁺) resin catalyzes efficient cationic endo-cyclization of γ- and δ-unsaturated alcohols to yield tetrahydro-(2 H)-pyrans and oxepanes. The merits of the present protocol are good yield of the products under mild conditions, simple workup, and reusability of the resin.

Keywords:

ACKNOWLEDGMENTS

We thank the Kelkar Education Trust and S. H. Kelkar Company for research support and encouragement.

Notes

^aSolvent A = toluene, B = no solvent, and C = dichloromethane.

^bResin–substrate ratio 1:10.

^cYield of the products were obtained by GC-MS.

^dRoom temperature.

^eMajor products are ocimene and allo-ocimene formed by dehydration.

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Amberlyst-15–Catalyzed Efficient Cyclization of γ- and δ-Unsaturated Alcohols: Green Synthesis of Oxygen Heterocycles

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Amberlyst-15–Catalyzed Efficient Cyclization of γ- and δ-Unsaturated Alcohols: Green Synthesis of Oxygen Heterocycles

Abstract

ACKNOWLEDGMENTS

Notes

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