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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]
Pages 74-80 | Received 25 Nov 2008, Published online: 09 Dec 2009
 
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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.

ACKNOWLEDGMENTS

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

Notes

a Solvent A = toluene, B = no solvent, and C = dichloromethane.

b Resin–substrate ratio 1:10.

c Yield of the products were obtained by GC-MS.

d Room temperature.

e Major products are ocimene and allo-ocimene formed by dehydration.

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