Unprecedented InCl3-catalyzed formation of cis-fused perhydrofuro[2,3-b]oxepines |
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| Authors: | J.S. Yadav B.V.S. ReddyG. Satheesh A. PrabhakarA.C. Kunwar |
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| Affiliation: | a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
b Centre for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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| Abstract: | 2-Methylindole and its N-substituted derivatives react smoothly with 2,3-dihydrofuran (DHF) in the presence of a catalytic amount of InCl3 under mild conditions to afford the corresponding 2-methyl-3-perhydrofuro[2,3-b]oxepin-4-yl-1H-indole derivatives in fairly good yields with high diastereoselectivity, while 3,4-dihydro-2H-pyran (DHP) affords exclusively 5,5-di(1H-3-indolyl)-1-pentanol derivatives in high yields under similar reaction conditions. |
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| Keywords: | indium reagents indoles cyclic enol ethers perhydrofuro[2,3-b]oxepines |
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