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Asymmetric total synthesis of (2S,3S)-3-hydroxypipecolic acid
โ Scribed by Subhash P. Chavan; Nilesh B. Dumare; Kishor R. Harale; Uttam R. Kalkote
- Publisher
- Elsevier Science
- Year
- 2011
- Tongue
- French
- Weight
- 313 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
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.
๐ SIMILAR VOLUMES
An asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid was accomplished in eight steps and 31% overall yield.
The stereochemical outcome of the Michael reaction between ethyl 4,4,4-trifluorocrotonate and a Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)aminolbenzophenone was found to be subjected to kinetic and thermodynamic control. Thus, under kinetically controlled conditions