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Synlett 2014; 25(15): 2213-2216
DOI: 10.1055/s-0034-1378538
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© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of (1S,2R)-1-Amino-2-methylcyclopropanephosphonic Acid: A Phosphonic Analogue of (–)-Norcoronamic Acid – Influence of Stereochemistry on Regioselectivity in Sulfoxide–Metal Exchange

Wanda H. Midura*
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, 90-363 Lodz Sienkiewicza 112, Poland   Fax: +48(42)6847126   eMail: whmidura@bilbo.cbmm.lodz.pl
,
Aneta Rzewnicka
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, 90-363 Lodz Sienkiewicza 112, Poland   Fax: +48(42)6847126   eMail: whmidura@bilbo.cbmm.lodz.pl
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Publikationsverlauf

Received: 27. April 2014

Accepted after revision: 25. Juni 2014

Publikationsdatum:
06. August 2014 (online)

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Abstract

Asymmetric synthesis of (–)-(1S,2R)-1-amino-2-methylcyclopropanephosphonic acid, a phosphonic analogue of (–)-norcoronamic acid was developed. The presence of the nitrile group as a precursor of the amino moiety, by changing stereoselectivity in the alkylation step, in consequence allowed to avoid 1,2-migration of a phosphoryl group on the cyclopropane ring and to obtain the required cyclopropylphosphonate of the retained structure and configuration.

Key words

cyclopropanes - ylides - amino acids - cyclopropyl sulfoxide - asymmetric synthesis

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
  • Supporting Information
 

  • References and Notes

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