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ortho-Directed metallation in the regiocontrolled synthesis of enantiopure 2- and/or 3-substituted (S)S-(p-tolylsulfinyl)-1,4-benzoquinones

✍ Scribed by M Carmen Carreño; JoséL García Ruano; Miguel A Toledo; Antonio Urbano

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 576 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00062-1

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✦ Synopsis

Enantiomerically pure (S)S-(p-tolylsulfinyl)-l,4-benzoquinones with alkyl and methoxy substituents at C-2 and/or C-3 are synthesized by CAN oxidation of adequately substituted (S)S-(p-tolylsulfinyl)-l,4-dimethoxyaromatic precursors 2 or 3. These compounds were obtained by ortho-directed metallation or bromo-metal exchange from the corresponding p-methoxyanisoles in a highly regiocontrolled manner.

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