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

作者：Reddy B V Subba^*; Venkateswarlu A; Sridevi B; Marumudi Kanakaraju; Kunwar A C; Gayatri G

来源：Organic and Biomolecular Chemistry, 2015, 13(9): 2669-2672.

DOI：10.1039/c4ob02347a

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.

• 出版日期2015