Synthesis of enantiopure (R,R)- and (S,S)-cis-2,3-propanoprolines

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2010
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Grygorenko, Oleksandr O.
Komarov, Igor V.
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10.1016/j.tetasy.2010.11.017
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Tetrahedron: Asymmetry ; 21 (2010), 23. - pp. 2868-2871. - Elsevier. - ISSN 0957-4166. - eISSN 1362-511X
Abstract
A novel approach to the synthesis of an enantiopure bicyclic proline analogue, hexahydrocyclopenta[b]pyrrole-6a(1H)-carboxylic acid (‘2,3-propanoproline’), has been developed. The method relied on tandem Strecker-nucleophilic cyclization reaction of 2-(2-bromoethyl)cyclopentanone. The overall synthetic scheme included six steps and resulted in 18% overall yield of both enantiomers of the title amino acid.
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ISO 690KOPYLOVA, Natalia, Oleksandr O. GRYGORENKO, Igor V. KOMAROV, Ulrich GROTH, 2010. Synthesis of enantiopure (R,R)- and (S,S)-cis-2,3-propanoprolines. In: Tetrahedron: Asymmetry. Elsevier. 21(23), pp. 2868-2871. ISSN 0957-4166. eISSN 1362-511X. Available under: doi: 10.1016/j.tetasy.2010.11.017
BibTex
@article{Kopylova2010-12Synth-52038,
  year={2010},
  doi={10.1016/j.tetasy.2010.11.017},
  title={Synthesis of enantiopure (R,R)- and (S,S)-cis-2,3-propanoprolines},
  number={23},
  volume={21},
  issn={0957-4166},
  journal={Tetrahedron: Asymmetry},
  pages={2868--2871},
  author={Kopylova, Natalia and Grygorenko, Oleksandr O. and Komarov, Igor V. and Groth, Ulrich}
}
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