Issue 9, 2015
From the journal:

Organic & Biomolecular Chemistry

A novel Prins cascade process for the stereoselective synthesis of oxa-bicycles†

B. V. Subba Reddy,*a   A. Venkateswarlu,a   B. Sridevi,a   Kanakaraju Marumudi,b   A. C. Kunwarb  and  G. Gayatric  

* Corresponding authors

a Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India
E-mail: basireddy@iict.res.in
Web: http://www.iictindia.org
Fax: +91-40-27160512

b Centre for NMR and Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India

c Centre for Molecular Modelling, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India

Abstract

E- and Z-9-Methyldeca-3,8-dien-1-ols undergo smooth cyclization with aldehydes in the presence of 20 mol% AgSbF6 under extremely mild conditions to generate the corresponding oxa-bicycles in good yields with excellent selectivity. In fact, E-olefin affords the trans-product exclusively, whereas the Z-olefin gives the cis-product predominantly. In the case of E- or Z-8-methylnona-3,8-dien-1-ol, the product is formed via the termination of Prins cyclization with an allylic C–H bond through olefin migration. The termination of Prins cyclization with tethered olefin is an unprecedented reaction, which provides a useful motif of various natural products.

Graphical abstract: A novel Prins cascade process for the stereoselective synthesis of oxa-bicycles

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DOI
https://doi.org/10.1039/C4OB02347A
Article type
Paper
Submitted
05 Nov 2014
Accepted
02 Jan 2015
First published
02 Jan 2015

Org. Biomol. Chem., 2015,13, 2669-2672

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A novel Prins cascade process for the stereoselective synthesis of oxa-bicycles

B. V. Subba Reddy, A. Venkateswarlu, B. Sridevi, K. Marumudi, A. C. Kunwar and G. Gayatri, Org. Biomol. Chem., 2015, 13, 2669 DOI: 10.1039/C4OB02347A

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