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Substituent effects in the selective reductive opening of epoxides with borohydrides in the presence of β-cyclodextrin

✍ Scribed by Joël Doussot; Alain Guy; Jean-Michel Siaugue; Clotilde Ferroud; Annie Fal Guières

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 103 KB
Volume: 11
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(1999)11:7<541::aid-chir5>3.0.co;2-g

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✦ Synopsis

The opening of ortho-substituted phenyl oxiranes by borohydrides is described both in aqueous and solid phases. Some remarkable differences in the regioselectivity and inversion of enantioselectivity of oxirane ring-opening are reported. The results obtained are compared with previous studies and have allowed some factors governing the reactivity, the regio- and stereoselectivity of this reaction to be evaluated. Preferential orientations of the substrate included inside the cyclodextrin are proposed from these results. Copyright 1999 Wiley-Liss, Inc.

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