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Dorizon P, Su G, Ludvig G, et al. Stereoselective Synthesis of Highly Functionalized Cyclopropanes. Application to the Asymmetric Synthesis of (1S,2S)-2,3-Methanoamino Acids. J Org Chem. 1999;64(13):4712-4724doi: 10.1021/jo982528g.
Dorizon, P., Su, G., Ludvig, G., Nikitina, L., Paugam, R., Ollivier, J., & Salaün, J. (1999). Stereoselective Synthesis of Highly Functionalized Cyclopropanes. Application to the Asymmetric Synthesis of (1S,2S)-2,3-Methanoamino Acids. The Journal of organic chemistry, 64(13), 4712-4724. https://doi.org/10.1021/jo982528g
Dorizon, Philippe, et al. "Stereoselective Synthesis of Highly Functionalized Cyclopropanes. Application to the Asymmetric Synthesis of (1S,2S)-2,3-Methanoamino Acids." The Journal of organic chemistry vol. 64,13 (1999): 4712-4724. doi: https://doi.org/10.1021/jo982528g
Dorizon P, Su G, Ludvig G, Nikitina L, Paugam R, Ollivier J, Salaün J. Stereoselective Synthesis of Highly Functionalized Cyclopropanes. Application to the Asymmetric Synthesis of (1S,2S)-2,3-Methanoamino Acids. J Org Chem. 1999 Jun 25;64(13):4712-4724. doi: 10.1021/jo982528g. PMID: 11674544.
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J Org Chem. 1999 Jun 25;64(13):4712-4724. doi: 10.1021/jo982528g.

Stereoselective Synthesis of Highly Functionalized Cyclopropanes. Application to the Asymmetric Synthesis of (1S,2S)-2,3-Methanoamino Acids.

The Journal of organic chemistry

Philippe Dorizon, Guifa Su, Gitte Ludvig, Lilyia Nikitina, Renée Paugam, Jean Ollivier, Jacques Salaün

Affiliations

  1. Laboratoire des Carbocycles (Associé au CNRS), Institut de Chimie Moléculaire d'Orsay, Bât. 420, Université de Paris-Sud, 91405 Orsay, France.

PMID: 11674544 DOI: 10.1021/jo982528g

Abstract

One-pot palladium(0)-catalyzed alkylation and S(N)(') cyclization of 1,4-dichlorobut-2-ene 1 by the anion of alpha-substituted carbonitriles 2a-d can provide highly functionalized cyclopropanes (E)-4a-d, diastereoselectivity, (de 88-100%). Several attempts to achieve the asymmetric synthesis of the 1-amino-2-ethenylcyclopropanecarbonitrile (E)-9, by means of this new procedure, i.e., using chiral palladium ligands, chiral aminoacetonitriles (-)- and (+)-12 (from 1-hydroxypinanone) or chiral allyl chlorides (4S)-20b-d and (4R)-20e (from (2S) ethyl lactate) have pointed up the reversibility of the palladium-catalyzed cyclization step, responsible for the low enantioselectivity observed (ee 88%) and provided the enantiomerically enriched 1-amino-2-propenylcyclopropanecarbonitrile (E)-22 (ee > 83%) suitable precursor of (1S,2S)-2,3-methanoamino acids.

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