[2+2]-Cycloaddition of Chlorosulfonyl Isocyanate to (Z)-Propenyl Ethers Bound to Polystyrene Resins by Alkylsulfonyl Linkers

Autor:	Barbara Grzeszczyk, Bartłomiej Furman, Marek Chmielewski, Robert Łysek
Rok vydání:	2004
Předmět:	Chlorosulfonyl isocyanate Propenyl Chemistry Organic Chemistry Diastereomer Alkylation Cycloaddition chemistry.chemical_compound Intramolecular force Polymer chemistry Organic chemistry Stereoselectivity Polystyrene Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2004:4177-4187
ISSN:	1099-0690 1434-193X
Popis:	The 3-O- and 5-O-(Z)-propenyl ethers derived from 1,2-O-isopropylidene-α-D-xylo- and glucofuranoses, respectively, were attached to the Merrifield, MPPC and NCPSC resins using alkylsulfonyl linkers. The [2+2]-cycloaddition of chlorosulfonyl isocyanate to the polymer-bound vinyl ethers followed by the intramolecular alkylation of the β-lactam nitrogen led to the formation of mixtures of the corresponding diastereomeric oxacephams or clavams with a low stereoselectivity. In the case of Merrifield and MPP resins, the β-lactams were accompanied by the corresponding oxetanes or oxiranes. Reactions performed using soluble polymer proceeded similarly to those carried out in solution. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Databáze:	OpenAIRE
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