Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure 3-Substituted (2R,3S)-Serine Methyl Esters

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1991
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Beulshausen, Tessa
Schöllkopf, Ulrich
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Zusammenfassung

The titanium derivative 2 of the bislactim ether 1 of cyclo(-LVal-Gly-) reacts with aldehydes and ketones 3 highly diastereoselectively to give the syn-addition products 4. Upon hydrolysis with diluted trifluoroacetic acid the compounds 4 yield besides methyl L-valinate the (2R,BS)-threo-serinme ethyl esters 5.

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540 Chemie
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Serine, 3-substituted, methyl esters, Bislactim ether method
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ISO 690BEULSHAUSEN, Tessa, Ulrich GROTH, Ulrich SCHÖLLKOPF, 1991. Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure 3-Substituted (2R,3S)-Serine Methyl Esters. In: Liebigs Annalen der Chemie. 1991, 1991(11), pp. 1207-1209. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.1991199101206
BibTex
@article{Beulshausen1991Asymm-9734,
  year={1991},
  doi={10.1002/jlac.1991199101206},
  title={Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure 3-Substituted (2R,3S)-Serine Methyl Esters},
  number={11},
  volume={1991},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={1207--1209},
  author={Beulshausen, Tessa and Groth, Ulrich and Schöllkopf, Ulrich}
}
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