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Reactions of 2,5-dihydro-2,5-dimethoxy-furan with phenylselenenylchloride: Regio- and stereocontrolled generation of highly functionalized C4 building-blocks

✍ Scribed by Franco D'Onofrio; Roberto Margarita; Luca Parlanti; Daniele Pernazza; Giovanni Piancatelli

Book ID: 104208170
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 440 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)10044-8

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✦ Synopsis

An efficient protocol for stereo-and regiocontrolled synthesis of small polyfunctional molecules is presented. The stereospecific addition of PhSeCI to 2,5-dihydro-2,5-dimethoxy-furan 1 in solvents, such as methylene chloride and methanol, gives cyclic and linear acetals 2 and 3, depending on the solvent used. Emphasis is given to the regiocontrolled hydrolysis of acetal groups for the preparation of stereodefined and highly functionalized C4 synthons, such as 8, 9 and 13.

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