Total regioselective and diastereospecific iodolysis of 2,3-epoxyamides promoted by SmI2: Synthesis of (2R*,3R*)- or (2R*,3S*)-2-hydroxy-3-iodoamides

Journal of Organic Chemistry

Volumn 69, Issue 20, 2004, Pages 6923-6926

  Concellón, José M ^a   Bardales, Eva ^a   Concellón, Carmen ^a   García Granda, Santiago ^a   Díaz, M Rosario ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; SAMARIUM COMPOUNDS; SUBSTITUTION REACTIONS; X RAY ANALYSIS;

ENOLATES; IODOLYSIS; REGIOSELECTIVITY; RING OPENING REACTIONS;

IODINE COMPOUNDS;

2 HYDROXY 3 IODOAMIDE; 2,3 EPOXYAMIDE; AMIDE; EPOXIDE; IODINE DERIVATIVE; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; HYDROLYSIS; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY ANALYSIS;

EID: 4644232204     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049021s     Document Type: Article

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41. 2, such as methanol (Hasagewa, E.: Curran, D. P. J. Org. Chem. 1993, 58, 5008) or HMPA (Inanaga, J.; Handa, Y.; Tabuchi, T.; Otsubo, J.; Yamaguchi, M.; Hanamoto, T. Tetrahedron Lett. 1991, 32, 6557). In addition, elimination reactions is also favored by higher temperatures. See ref 18.
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47. 2 to the 2,3-epoxyamides is favored by the electron-donating capacity of the nitrogen.
48. 3, a complex mixture of products, containing the corresponding iodohydrin as minor product, was obtained.
49. 2-promoted ring opening of 2,3-epoxyesters has been proposed in ref 15d.
50. Concellón, J. M.; Bardales, E. J. Org. Chem. 2003, 68, 1585.