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Synthesis 2000; 2000(1): 127-134
DOI: 10.1055/s-2000-6237
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Enantioselective Sharpless Dihydroxylation of Vinylic Aromatic Heterocycles

Christophe M. G. Philippo* , Patrick Mougenot, Alain Braun, Gérard Defosse, Stéphanie Auboussier, Philippe R. Bovy
  • *Synthélabo Recherche, Preclinical Research, Internal Medecine Department of Chemistry, 10, rue des Carrières, F-92504 Rueil-Malmaison Cedex, France; Fax +33 (1) 41 39 13 03; E-mail: Cphilipp@rueil.synthelabo.fr
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Publication Date:
31 December 2000 (online)

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Asymmetric dihydroxylation (AD) with an AD-mix reagent was conducted on a series of terminal olefins possessing an extended heteroaromatic group. Good yields and high enantioselectivities were observed in most instances. However, the steric hindrance resulting from neighboring substituents on the aromatic heterocycle can interfere during the course of the dihydroxylation. The effects of voluminous groups such as t-Boc, t-BDMS or adamantylmethyl were evaluated.

enantioselective Sharpless dihydroxylation - aromatic heterocycles - optical purity - steric hindrance