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InCl3-catalyzed stereoselective synthesis of C-glycosyl heteroaromatics

โœ Scribed by J.S Yadav; B.V.S Reddy; J.V Raman; N Niranjan; S Kiran Kumar; A.C Kunwar

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
239 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Glycals react smoothly with furan in the presence of a catalytic amount of indium trichloride at ambient temperature to afford predominantly the C-3-substituted glycals in high yields. Other heteroaromatics including 2-benzyloxymethylfuran, thiophene and N-Boc protected indole afford exclusively C-1-glycosides in good yields with high b-selectivity under similar reaction conditions.

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โœ J.S Yadav; B.V.S Reddy; Sunny Abraham; G Sabitha ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 123 KB

A variety of N-tosylaziridines undergo ring opening with pyrrole, furan, thiophene and indole in the presence of a catalytic amount of indium trichloride at ambient temperature to afford the corresponding b-aminoheterocycles in good yields with high regioselectivity.