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Asymmetric Synthesis of Methyl (2R,3S)-2-Amino-3-cyclopropyl-3-hydroxyalkanoates via Diastereoselective Simmons-Smith Reactions

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1991

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Schöllkopf, Ulrich
Tiller, Thomas

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Published

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Liebig's Annalen der Chemie. 1991(9), pp. 857-860. ISSN 0170-2041

Zusammenfassung

The cyclopropanation of the bislactim ethers 3 with diiodo-hymethanes and diethylzinc proceeds in good yields and with high diastereoselectivities, affording the cyclopropyl bislactim ethers 6. Protection of the hydroxy group and subsequent hydrolysis furnish virtually enantiomerically and diastereo merically pure methyl (2R,3S)-2-amino-3-cyclopropyl-3-droxyalkanoates 8. The bislactim ethers of type 3 are obtained by a known method diastereomerically pure, starting from the bislactim ether of cycle(-L-Val-Gly-).

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Fachgebiet (DDC)
540 Chemie

Schlagwörter

Serine, 3-cyclopropyl derivatives, Simmons-Smith reaction, diastereoselective, Bislactim ether method

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ISO 690GROTH, Ulrich, Ulrich SCHÖLLKOPF, Thomas TILLER, 1991. Asymmetric Synthesis of Methyl (2R,3S)-2-Amino-3-cyclopropyl-3-hydroxyalkanoates via Diastereoselective Simmons-Smith Reactions. In: Liebig's Annalen der Chemie. 1991(9), pp. 857-860. ISSN 0170-2041
BibTex
@article{Groth1991Asymm-10064,
  year={1991},
  title={Asymmetric Synthesis of Methyl (2R,3S)-2-Amino-3-cyclopropyl-3-hydroxyalkanoates via Diastereoselective Simmons-Smith Reactions},
  number={9},
  issn={0170-2041},
  journal={Liebig's Annalen der Chemie},
  pages={857--860},
  author={Groth, Ulrich and Schöllkopf, Ulrich and Tiller, Thomas}
}
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