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Synlett 1999; 1999(12): 1903-1906
DOI: 10.1055/s-1999-3176
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Synthesis of 2-Amino-2-methyl-4-phosphonobutanoic Acids by Conjugate Addition of Lithiated Bislactim Ether Derived from Cyclo[Ala-d-Val] to Vinylphosphonates

María Ruiz* , M. Carmen Fernández, Susana Conde, Aniana Díaz, José M. Quintela
  • *Departamento de Quìmica Fundamental e Industrial, Facultade de Ciencias, Universidade da Coruña. Campus A Zapateira s/n, 15071 A Coruña, Spain; Fax 34-9 81-16 70 65; E-mail: vocqfo@udc.es
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Publication Date:
31 December 1999 (online)

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Face-selective conjugate addition of lithiated Schöllkopf's bislactim ether derived from cyclo[Ala-d-Val] 4 to prochiral vinylphosphonates 5a-c allows a direct and stereocontrolled access to optically pure MAP4 analogues, the 2-amino-2-methyl-4-phosphonobutanoic acid derivatives 12-15. The relative stereochemistry was assigned from NMR studies of the cyclic derivatives 16 and 17. Eight-membered transition states are invoked to rationalize the stereochemical outcome of the additions.

phosphonobutanoic acids - α-methyl α-amino acids - conjugate addition - stereoselective synthesis - vinylphosphonates