Enantioselective synthesis of α-hydroxy-β-amino acids from α-amino acids mediated by sulfoxides

Tetrahedron

Volumn 63, Issue 42, 2007, Pages 10521-10527

  Sánchez Obregón, Rubén ^a   Salgado, Fernando ^a   Ortiz, Benjamín ^a   Díaz, Eduardo ^a   Yuste, Francisco ^a   Walls, Fernando ^a   García Ruano, José L ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO HYDROXYBUTANOIC ACID; ALANINE DERIVATIVE; ALPHA AMINO ACID; ALPHA HYDROXY BETA AMINO ACID; AMINO ACID DERIVATIVE; BUTYRIC ACID; COLLIDINE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; PRIORITY JOURNAL; PUMMERER REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34548405280     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.072     Document Type: Article

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36. Amide oxygen attack on sulfur resulting in the formation of a six-membered ring intermediate has also been suggested as the second step in the evolution of β-amino sulfoxides (see. García Ruano J.L., Alemán J., Prado M., and Fernández I. J. Org. Chem. 69 (2004) 4454 ) as alternative to the amide nitrogen attack resulting in the azathiacyclobutane suggested by Zanda in Ref. 15d. This proposal was based on the higher stability of a 6-membered over a 4-membered cyclic systems. The attack of the nitrogen to the sulfur is the only able to explain the results obtained from the γ-amino sulfoxides described in this work because the attack of the oxygen would not explain the formation of compounds 6 or 7, bearing the S-N bond. Taking into account that Zanda et al. have also isolated the sulfenamides from the NOPR of (Ref. 15d), an azathiacyclobutane intermediate resulting in the nitrogen attack seem to be the most probable intermediate also for β-amino sulfoxides
37. Similar results were obtained starting from 5a.