Asymmetric synthesis of α-acetylenic epoxides

Tetrahedron Asymmetry

Volumn 10, Issue 5, 1999, Pages 947-955

  Sánchez Obregón, Rubén ^a   Ortiz, Benjamin ^a   Walls, Fernando ^a   Yuste, Francisco ^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

ALPHA ACETYLENIC EPOXIDE; EPOXIDE; ETHYLENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0342621309     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00079-8     Document Type: Article

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44. 2 (Carreño, C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1992, 57, 6870). It seems that decreasing the temperature below -20°C makes the chelation difficult and lower stereoselective cycloadditions are observed.
45. These values are only slightly lower than those usually observed for alkyl keto sulfoxides, which could be attributed to the fact that the extended conjugation of compounds 2 decreases the ability of the carbonyl to become chelated.