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Synthesis of both enantiomers of trans 3-hydroxypipecolic acid

✍ Scribed by Christine Greck; Franck Ferreira; Jean Pierre Genêt

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
188 KB
Volume
37
Category
Article
ISSN
0040-4039

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An alternative stereoselective synthesis
An alternative stereoselective synthesis of trans-(2R,3R)-3-hydroxypipecolic acid
✍ Mansour Haddad; Marc Larchevêque 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 71 KB

The enantioselective synthesis of trans-(2R,3R)-3-hydroxypipecolic acid 1b is presented, starting from O-protected methyl mandelate as chiral source. The synthesis involved a regioselective intramolecular nucleophilic substitution of an azido epoxide as the key step .

Asymmetric total synthesis of (2S,3S)-3-
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✍ Subhash P. Chavan; Nilesh B. Dumare; Kishor R. Harale; Uttam R. Kalkote 📂 Article 📅 2011 🏛 Elsevier Science 🌐 French ⚖ 313 KB

A synthetic route to (2S,3S)-3-hydroxypipecolic acid was achieved from readily available nonchiral pool starting material cis-2-butene-1,4-diol and involved Claisen orthoester rearrangement, Sharpless asymmetric dihydroxylation and intramolecular lactamisation of azido lactone as the key steps.