Highly asymmetric Pummerer-type reaction induced by ethoxy vinyl esters

Ethoxy vinyl esters (EVE: 2) were efficient reagents for promoting the asymmetric Pummerer reaction with high enantioselectivity and high yield in contrast to the generally used acid anhydrides. Increasing the electron-donating ability on the R function in EVE 2 tended to increase enantioselectivity...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 8; no. 2; pp. 303 - 310
Main Authors Shibata, Norio, Matsugi, Masato, Kawano, Noriyuki, Fukui, Seiji, Fujimori, Chino, Gotanda, Kentoku, Murata, Kenji, Kita, Yasuyuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.01.1997
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ALCOHOLS
SULFOXIDES
ACYLATION
AMINES
OXAUNOMYCIN DERIVATIVES
EFFICIENT SYNTHESIS
ACETIC-ANHYDRIDE
1-ETHOXYVINYL ESTERS
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Summary:Ethoxy vinyl esters (EVE: 2) were efficient reagents for promoting the asymmetric Pummerer reaction with high enantioselectivity and high yield in contrast to the generally used acid anhydrides. Increasing the electron-donating ability on the R function in EVE 2 tended to increase enantioselectivity. Consequently, effective asymmetric rearrangements were achieved using EVEs 2b,c bearing a methoxybenzoyloxy function. In Pummerer-type reaction, effective 1,2-chiral transfer was achieved by the use of EVE bearing a powerful electron-donating function.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(96)00510-1