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Synlett 1998; 1998(2): 195-197
DOI: 10.1055/s-1998-1596
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Iodine(III)-Initiated Bromoacetoxylation of Olefins

Md. Abul Hashem* , Alexander Jung, Monika Ries, Andreas Kirschning
  • *Institut für Organische Chemie der Technischen Universität Clausthal, Leibnizstraße 6, D-38678 Clausthal-Zellerfeld, Germany; Fax [int] (+)-(0) 53 23-72 28 58; E-mail: andreas.kirschning@tu-clausthal.de
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Publication Date:
31 December 2000 (online)

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A new and mild method for the bromoacetoxylation of olefins is presented, which is initiated by iodine(III). α-Acetoxy bromides 6-11 are generated from olefins 5 in the presence of tetraethylammonium bromide (1) and (diacetoxyiodo)benzene (2). The 1,2-addition to carbohydrate-derived enol ethers results in 2-deoxy-2-bromo-pyranosyl acetates which are versatile glycosyl donors for the synthesis of 2'-deoxy-2'-bromo glycosides 16.

addition - glycosidation - hypervalent - olefins