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A Short, Gram-Scale Synthesis of 2,5-Disubstituted Furans

โœ Scribed by Chang, Stanley; Desai, Saheena; Leznoff, Daniel B.; Merbouh, Nabyl; Britton, Robert

Book ID
120360633
Publisher
John Wiley and Sons
Year
2013
Tongue
English
Weight
331 KB
Volume
2013
Category
Article
ISSN
1434-193X

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๐Ÿ“œ SIMILAR VOLUMES

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The dianion derived from the oxime of furfuraldehyde (1) reacts with electrophiles at the 5-position of the furan ring; subsequent hydrol$is of the oxime provides a useful method for the synthesis of 2,5\_disubstituted furans.

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A novel approach to chiral 2,5-disubsfituted pyrrolidines, starting from chiral 2-phenylglycinol, 1,5-dimethoxytetrahydrofiuan, and benzotriazole, involves the diastereoselective substitution by Grignard reagents of a benzotriazolyl group in a crystalline intermediate obtained in high yield.