(Z)-Selective Wittig and Corey-Chaykovsky reactions of propargyl ylides using trialkylgallium bases

Tetrahedron Letters

Volumn 49, Issue 21, 2008, Pages 3492-3495

  Nishimura, Yoshio ^a   Shiraishi, Takao ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; ALKYL GROUP; BASE; CARBONYL DERIVATIVE; EPOXIDE; GALLIUM; KETONE; METAL; PHOSPHONIUM DERIVATIVE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON TRANSPORT; STEREOCHEMISTRY; WITTIG REACTION;

EID: 43049106418     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.086     Document Type: Article

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45. 3 did not give epoxide 6 by reacting at rt, and formed decomposed products derived from 4. In contrast, butyllithium and LDA gave 6 in 43% (Z:E = 98:2) and 47% (Z:E = 97:3) yields, respectively. The origin of the metal effect on the stereochemistry is a subject of interest in future.