Issue 7, 2012
From the journal:

Organic & Biomolecular Chemistry

Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation†

B. V. Subba Reddy,*a   Prashant Borkar,a   J. S. Yadav,*a   P. Purushotham Reddy,b   A. C. Kunwar,b   B. Sridharc  and  René Gréed  

* Corresponding authors

a Division of Organic Chemistry-1, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, India
E-mail: basireddy@iict.res.in, yadavpub@iict.res.in
Fax: (+)91 40 27160512

b Centre for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, India

c Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, India

d Université de Rennes 1, Laboratoire SCR, CNRS UMR 6226, Avenue du Général Leclerc, Rennes Cedex, France

Abstract

1-Benzyl ethers of (E)- and (Z)-hex-3-en-1,6-diols and hept-3-en-1,7-diols undergo a smooth oxidative cyclization with DDQ in the presence of In(OTf)3 through a sequential C–H bond activation and an intramolecular Prins cyclization to afford the corresponding trans- and cis-fused hexahydro-2H-furo[3,2-c]pyrans and octahydropyrano[4,3-b]pyrans respectively in good yields with an excellent stereoselectivity. Aryl tethered homoallylbenzyl ethers such as benzyl ethers of (E)- and (Z)-6-arylhex-3-enyl alcohols undergo a tandem Prins/Friedel–Crafts cyclization in the presence of stoichiometric amounts of DDQ and SnCl4via the benzylic C–H bond activation to furnish the corresponding trans- and cis-fused hexahydro-1H-benzo[f]isochromenes in good yields with complete stereoselectivity.

Graphical abstract: Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation

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Article information

DOI
https://doi.org/10.1039/C1OB06489D
Article type
Paper
Submitted
30 Aug 2011
Accepted
03 Nov 2011
First published
03 Nov 2011

Org. Biomol. Chem., 2012,10, 1349-1358

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Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation

B. V. Subba Reddy, P. Borkar, J. S. Yadav, P. Purushotham Reddy, A. C. Kunwar, B. Sridhar and R. Grée, Org. Biomol. Chem., 2012, 10, 1349 DOI: 10.1039/C1OB06489D

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