Simple protocol for enhanced (E)-selectivity in Julia-Kocienski reaction

Tetrahedron Letters

Volumn 52, Issue 18, 2011, Pages 2348-2352

  Pospíšil, Jiří ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Chelation; Julia Kocienski reaction; Olefins; Selectivity

Indexed keywords

ALKENE; CHELATING AGENT;

ARTICLE; CHEMICAL REACTION; CLINICAL PROTOCOL; OLEFINATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 79953280606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.086     Document Type: Article

References (17)

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12. It was also reported that the addition of 18-crown-6 (for KHMDS promoted coupling) might increase the reaction selectivity if an α O-alkyl substituted aldehyde was used as a reaction substrate. It was suggested that the presence of 18-crown-6 disabled possible stabilization of the adduct and so, prevented the retro addition reaction. K. Ishigami, H. Watanabe, and T. Kitahara Tetrahedron 61 2005 7546 7553
13. For complete reaction optimization table see Table S-1.
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17. 4, filtered, and the solvents were evaporated under reduced pressure. The residue was purified by flash column chromatography (P.E./EtOAc = 100:0→20:1) yielding 54.4 mg (82%) of colorless oil ((E/Z) = >50:1).