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Reaction of homoallylic alcohols with NaIO4/NaHSO3 reagent—synthesis of alkyl substituted tetrahydrofuran derivatives

✍ Scribed by Yoshio Okimoto; Daisuke Kikuchi; Satoshi Sakaguchi; Yasutaka Ishii

Book ID: 104211364
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 63 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01819-0

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✦ Synopsis

Treatment of homoallylic alcohols with NaIO 4 /NaHSO 3 reagent in aqueous t-BuOH under mild conditions produced tetrahydrofuran derivatives together with iodohydrins in a stereospecific manner. The reaction pathways of the formation of tetrahydrofurans from trans-and cis-homoallylic alcohols were found to be different. The present method provides a new approach to various alkylated tetrahydrofuran derivatives.

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