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Issue 32, 2014
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InCl3-catalyzed Prins bicyclization for the synthesis of spirotetrahydropyran derivatives

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Abstract

A novel InCl3 catalyzed Prins bicyclization strategy has been developed for the synthesis of tetrahydro-3H-spiro[benzo[b][1,4]dioxine-2,4′-pyran] and hexahydrospiro[benzo[b][1,4]oxazine-2,4′-pyran] derivatives. The spirocyclization of 2-(4-hydroxy-2-methylenebutoxy)phenol with aldehyde proceeds at room temperature with high diastereoselectivity, whereas the similar cyclization with N-(4-hydroxy-2-methylenebutyl)-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide requires −20 °C to afford the product with good diastereoselectivity.

Graphical abstract: InCl3-catalyzed Prins bicyclization for the synthesis of spirotetrahydropyran derivatives

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Publication details

The article was received on 20 Feb 2014, accepted on 24 Mar 2014 and first published on 26 Mar 2014


Article type: Communication
DOI: 10.1039/C4RA01503G
RSC Adv., 2014,4, 16739-16742

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    InCl3-catalyzed Prins bicyclization for the synthesis of spirotetrahydropyran derivatives

    B. V. S. Reddy, S. Jalal and K. K. Singarapu, RSC Adv., 2014, 4, 16739
    DOI: 10.1039/C4RA01503G

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