Novel generation and cycloaddition of N-silylated azomethine ylides from α-silylimidates and trifluorosilane

Tetrahedron

Volumn 55, Issue 45, 1999, Pages 12969-12976

  Washizuka, Ken Ichi ^a   Minakata, Satoshi ^a   Ilhyong, Ryu ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; SILANE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SYNTHESIS; TECHNIQUE;

EID: 0033527805     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00805-4     Document Type: Article

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34. As we reported in reference 11, in the reaction of dimethyl maleate and the azomethine ylide generated from α-silylamide 16 by 1,4-silatropic shift, epimerization at 3-position of the cycloadduct occurred since the hydrogen at 3-position is highly acidic. From this result, in this work, we did not perform the cycloaddition with dimethyl maleate to avoid a complication of the stereochemistry.