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Asymmetric synthesis of syn and anti 1,2-diols from diethyl oxalate using the stereoselective sulfoxide directed reduction of 1,2-diketone derivatives

✍ Scribed by Guy Solladié; Gilles Hanquet; Irene Izzo; Robyn Crumbie

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
229 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new chiral Wittig reagent, a 13-keto-3,-(S)-hydroxy-f-(R)-p-tolylsulfinyl phosphonate, readily made from ethyl oxalate and stereoselective sulfoxide mediated reduction of the resulting 13-ketosulfoxide, was used to prepare enantiomerically pure syn and anti 1,2-diols.

This method was applied to the enantioselective synthesis of two acetogenin derivatives, (-)-(R,R)-muricatacin and its epimer (-)-(R,S)-epi-muricatacin.

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Stereoselective sulfoxide directed reduc
Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols
✍ Guy Solladié; Gilles Hanquet; Catherine Rolland 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 196 KB

A new route to enantiopure syn and anti 1,2-diols is described from oxalyl-di-(Nmethyl-N-methoxyamide) via the corresponding ~-ketosulfoxide. This is the first report of the stereoselective reduction ofaT--keto-~-hydroxysulfoxide.