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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 10
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Original Articles

A One-Pot Synthesis of trans-N-Alkylaziridine-2-carboxylates from Amino Alcohol Esters

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Pages 1472-1480 | Received 23 Jan 2010, Published online: 30 Mar 2011

REFERENCES

  • Sengupta , S. ; Mondal , S. InCl3-catalyzed reactions of ethyl diazoacetate with aldimines: A highly diastereoselective synthesis of cis-aziridine carboxylates . Tetrahedron Lett. 2000 , 41 , 6245 – 6248 , and references therein .
  • Yadav , J. S. ; Reddy , B. V. S. ; Rao , M. S. ; Reddy , P. N. LiClO4-catalyzed highly diastereoselective synthesis of cis-aziridine carboxylates . Tetrahedron Lett. 2003 , 44 , 5275 – 5278 .
  • (a) Osborn , H. M. I. ; Sweeney , J. The asymmetric synthesis of aziridines . Tetrahedron: Asymmetry 1997 , 8 , 1693 – 1715 ; (b) Na , Y. ; Wang , S. ; Kohn , H. 7-N-(Mercaptoalkyl)mitomycins: Implications of cyclization for drug function . J. Am. Chem. Soc. 2002 , 124 , 4666 – 4677 .
  • Olafsson , B. ; Wijtmans , R. ; Somfai , P. Synthesis of N-H vinylaziridines: A comparative study . Tetrahedron 2002 , 58 , 5979 – 5982 .
  • Thabur , V. V. ; Sudalai , A. N-Bromoamides as versatile catalysts for aziridination of olefins using chloramines-T . Tetrahedron Lett. 2003 , 44 , 989 – 992 , and references therein .
  • (a) Lee , S.-H. ; Han , T.-D. ; Yu , K. ; Ahn , K.-H. Aziridination of imines mediated by copper catalysts. Bull Korean Chem. Soc. 2001, 22(5), 449–450; (b) Lee , K.-D. ; Suh , J.-M. ; Park , J.-H. ; Ha , H.-J. ; Choi , H. G. ; Park , C. S. ; Chang , J. W. ; Lee , W. K. ; Dong , Y. ; Yun , H. New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates. Tetrahedron 2001, 57, 8267–8276, and references therein.
  • Cainelli , G. ; Panunzio , M. ; Giacomini , D. Studies on N-metallo imines: Synthesis of N-unsubstituted aziridines from N-trimethylsilyl imine and lithium enolates of α-haloesters . Tetrahedron Lett. 1991 , 31 , 121 .
  • (a) Pfister , J. R. A one-pot synthesis of aziridines from 2-aminoethanols . Synthesis 1984 , 969 – 970 ; (b) Kelly , J. W. ; Eskew , N. L. ; Evans , S. A. Cyclodehydration of N- and C-substituted β-amino alcohols to the corresponding aziridines with diethoxytriphenyl-phosphorane . J. Org. Chem. 1986 , 51 , 95 .
  • (a) Thijs , L. ; Porskamp , J. J. M. ; Van Loon , A. A. W. M. ; Deks , M. P. W. ; Feentra , R. W. ; Legters , J. ; Zwanenburg , B. Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate . Tetrahedron 1990 , 46 ( 7 ), 2611 – 2622 ; (b) Zwanenburg , B. ; Thijs , L. Aziridine and azirine carboxylic esters . Pure Appl. Chem. 1996 , 68 ( 3 ), 735 – 738 .
  • Nakagawa , Y. ; Tsuno , T. ; Nakajima , K. ; Iwai , M. ; Hawai , H. Studies on hydroxyl amino acids, IV: Synthesis of several peptides containing aziridinecarboxylic acid derived from the corresponding hydroxyl amino acid derivatives . Bull. Chem. Soc. Jpn. 1972 , 45 , 1162 .
  • Nakajima , K. ; Takai , F. ; Tanaka , T. ; Okawa , K. Studies on aziridine-2-carboxylic acid, I: Synthesis of the optically active L-aziridine-2-carboxylic acid and its derivatives . Bull. Chem. Soc. Jpn. 1978 , 51 , 1577 .
  • Wakamiya , T. ; Shimbo , K. ; Shiba , T. ; Nakajima , K. ; Neya , M. ; Okawa , K. Synthesis of threo-3-methylcysteine from threonine . Bull. Chem. Soc. Jpn. 1982 , 55 , 3878 .
  • Kuyl-Yehiskiely , E. ; Ladder , G. A. ; Vander Maul , G. A. ; Van Boom , J. H. One-step synthesis of optically active benzyl N-trityl-L-aziridine-2-carboxylic esters . Tetrahedron Lett. 1992 , 33 , 3013 .
  • (a) Chang , J. W. ; Bae , J. H. ; Shin , S.-H. ; Park , C. S. ; Choi , D. ; Lee , W. K. Synthesis of substituted (D)-phenylalanine derivatives by regioselective reduction of enantiomerically pure cis-2,3-disubstituted aziridines . Tetrahedron Lett. 1998 , 39 , 9193 – 9196 , and references therein ; (b) Willems , J. G. H. ; Hersmis , M. C. ; De Gelder , R. ; Smits , J. M. M. ; Hammink , J. B. ; Dommerholt , F. J. ; Thijs , L. ; Zwanenburg , B. Synthesis and crystal structure of enantiopure N-tritylaziridin-2-yl-methanols from L-serine and L-threonine . J. Chem. Soc. Perkin Trans. 1 1997 , 963 – 967 .
  • Ould Elemine , B. ; Besbes , R. ; Ennigrou , M. R. Straightforward synthesis of 1,2-amino phosphate diesters and application to the synthesis of novel 1,2-amino ether diesters . Synth. Commun. 2010 , 40 , 64 – 73 .
  • Besbes , R. ; Ennigrou , M. R. A simple and direct synthesis of erythro-β-amino-α-hydroxy esters from trans-β-phenylglycidic ester . Synth. Commun. 2004 , 34 ( 12 ), 2185 – 2194 .
  • Ould Elemine , B. ; Besbes , R. ; Ennigrou , M. R. Pratical preparation of β-amino-α-hydroxy diesters: Key intermediates for 1,4-oxazin-2-ones . Synth. Commun. 2007 , 37 , 3989 – 4004 .
  • Moureu , H. ; Chovin , P. ; Petit , L. Action des amines primaries et secondaires sur les derivés bromés des esters α,β-éthyléniques, IV: Dérivés de l'acide éthylène imine carboxylique-3 et esters α-aminés α,β-éthyléniques . Bull. Soc. Chim. 1955 , 1573 .

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