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Synthesis of7-Substituted 5-Dethia-5-oxacephams via [2+2]Cycloaddition of Chlorosulfonyl Isocyanate to Sugar Vinyl Ethers

Łysek R., Furman B., Kałuża Z., Chmielewski M.

Polish Journal of Chemistry

2000

Vol. 74, nr 1

51-60

Subsequent transformations of adducts consisting in detritylation, tosylation of a terminal hydroxy group and intramolecular alkylation of the nitrogen atom give corresponding tetracyclic 5-oxacephams.

[2+2]Cycloaddition of Chlorosulfonyl Isocyanate to Chiral Vinyl Ethers

Furman B., Kałuża Z., Łysek R., Chmielewski M.

Polish Journal of Chemistry

1999

vol. 73 nr 1

43-54

The asymmetric [2+2]cycloadditions of chlorosulfonyl isocyanate to vinyl ethers derived from sugars and hydroxy acids are presented. The account focuses on various aspects of the cycloaddition and on the transformations of the resulting [2+2]cycloadducts into clavams and 1-oxacephams. In order to rationalize the results of direction and magnitude of [2+2]cycloaddition, the stereochemical models of this reaction are discussed.