Stereocontrolled synthesis of (2S *,3R*,4R*)-4-hydroxy-3-methylproline using a silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement
- 16 January 2001
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 267-269
- https://doi.org/10.1039/b007586h
Abstract
The first racemic synthesis of the non-proteinogenic amino acid (2S,3R,4R)-4-hydroxy-3-methylproline (1) has been achieved via iodolactonisation of an unnatural amino acid derivative 4. The relative stereochemistry was derived from an efficient silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement of 2.Keywords
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