Synlett

Synthesis and Synthetic Applications of α, β-Dideuterio-α-amino Esters Promoted by Samarium Diiodide

JM Concellón, H Rodríguez-Solla, C Concellón…

Index: Concellon, Jose M.; Rodriguez-Solla, Humberto; Concellon, Carmen; Tuya, Paula Synlett, 2008 , # 3 p. 402 - 404

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Abstract

Abstract A new, easy, and high-yielded route to isotopically labeled amino acid derivatives is reported. This process takes place through a SmI 2-promoted 1, 4-reduction of a variety of dehydroamino esters in the presence of D 2 O. The dideuterio amino esters were transformed into other dideuterated compounds such as a-amino acids and 1, 2-amino alcohols. A mechanism to explain the 1, 4-reduction process is also proposed.

… samarium diiodide: asymmetric synthesis of (2 S, 3 R)-and (2 S, 3 S)-[2-2 H, 3-2 H]-leucine-(S)-phenylalanine dipeptides and (2 S, 3 R)-[2-2 H, 3-2 H]-phenylalanine …

[Davies, Stephen G.; Rodriguez-Solla, Humberto; Tamayo, Juan A.; Cowley, Andrew R.; Concellon, Carmen; Garner, A. Christopher; Parkes, Alastair L.; Smith, Andrew D. Organic and Biomolecular Chemistry, 2005 , vol. 3, # 8 p. 1435 - 1447]

Catalytic asymmetric hydrogenation of methyl (E)-and (Z)-2-acetamido-3-alkylacrylates

[Scott, John W.; Keith, Dennis D.; Nix, George; Parrish, David R.; Remington, Stuart; et al. Journal of Organic Chemistry, 1981 , vol. 46, p. 5086 - 5093]

Synthesis of e rythro-α-Amino β-hydroxy Carboxylic Acid Esters by Diastereoselective Photocycloaddition of 5-Methoxyoxazoles with Aldehydes

[Griesbeck, Axel G.; Bondock, Samir; Lex, Johann Journal of Organic Chemistry, 2003 , vol. 68, # 26 p. 9899 - 9906]