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Enantioselective synthesis of α-hydroxyacids through oxidation of terminal alkenes with AD-mix/TEMPO

✍ Scribed by F Javier Aladro; Francisco M Guerra; F Javier Moreno-Dorado; Jesús M Bustamante; Zacarı́as D Jorge; Guillermo M Massanet

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
159 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

α-Hydroxyacids can be enantioselectively prepared by means of a two-step oxidation process, involving first the asymmetric dihydroxylation of a terminal alkene and subsequent oxidation with TEMPO/NaOCl/NaClO 2 in good to excellent yields. No fragmentation of the glycol intermediate was detected.

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Enantioselective synthesis of threo-α,β-
Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents
✍ Tsutomu Yokomatsu; Takehiro Yamagishi; Kenji Suemune; Yoshinori Yoshida; Shirosh 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 969 KB

Asymmetric dihydroxylation (AD) of 1 (E)-alkenylphosphonates with an AD-m/x -ct or -~ reagent was examined to give a series of optically active threo-ot,~-dihydroxyphosphonates. Good enantioselectivity (>88% ee) was observed in the AD reaction of l(E)-alkenylphosphonates with conjugated aromatic sub