Amberlyst-15-Catalyzed Novel Synthesis of Tetrahydropyranols

Jhillu S. Yadav; Basi V. Subba Reddy; Korapala Chandra Sekhar; Duwuru Gunasekar

doi:10.1055/s-2001-13412

PAPER

Amberlyst-15-Catalyzed Novel Synthesis of Tetrahydropyranols [1]

Jhillu S. Yadav*^a, Basi V. Subba Reddy^a, Korapala Chandra Sekhar^a, Duwuru Gunasekar^b
^a Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India
^b Department of Chemistry, Sri Venkateswara University, Tirupati-517 502, India
Fax: +91(040)7170512; e-Mail: yadav@iict.ap.nic.in;

Abstract

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Abstract

The cross-coupling reaction of homoallyl alcohols with aldehydes in the presence of Amberlyst-15 resulted in the formation of 4-hydroxy-2,6-disubstituted tetrahydropyrans in high yields with high diastereoselectivity. The stereochemistry of these products was assigned with the assistance of coupling constants and nOe studies.

Key words

Amberlyst-15 - Prins cyclization - homoallyl alcohols - tetrahydropyranols

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References

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