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Synthesis 2001(6): 0885-0888
DOI: 10.1055/s-2001-13412
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Jhillu S. Yadav*a, Basi V. Subba Reddya, Korapala Chandra Sekhara, Duwuru Gunasekarb
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;
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Publication History

Received 4 January 2001
Publication Date:
24 September 2004 (online)

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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

1

IICT Communication No. 4701.

1

IICT Communication No. 4701.