A novel Prins cascade process for the stereoselective synthesis of oxa-bicycles
B V Subba Reddy1, A Venkateswarlu, B Sridevi
1Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India. basireddy@iict.res.in.
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.
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