Cycloadditions of cephalosporins. The formation of [4+2] adducts with 5-membered heterocycles

The cephalosporin triflate 1, and its sulfoxides 4 and 5, react with furan in the presence of a base to give [4 + 2] cycloadducts; the regiochemistry of the addition is determined by the oxidation state of the cephalosporin.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 59; no. 7; pp. 1606 - 1607
Main Authors Elliott, Richard L, Nicholson, Neville H, Peaker, Fiona E, Takle, Andrew K, Tyler, John W, White, Janet
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.1994
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Furan
Sulfur nitrogen heterocycle
Cycloaddition
Cephalosporin derivatives
Base catalysis
Oxygen sulfur nitrogen heterocycle
Regioselectivity
Lactam
Bicyclic compound
Sulfoxide
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Summary:The cephalosporin triflate 1, and its sulfoxides 4 and 5, react with furan in the presence of a base to give [4 + 2] cycloadducts; the regiochemistry of the addition is determined by the oxidation state of the cephalosporin.
Bibliography:ark:/67375/TPS-Q3CZ4R3Q-Z
istex:122348FAF0229FF4923218FE9F998CF09335E6B9
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00086a007