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[2+2]‐Cycloaddition of Chlorosulfonyl Isocyanate to ( Z )‐Propenyl Ethers Bound to Polystyrene Resins by Alkylsulfonyl Linkers
Author(s) -
Łysek Robert,
Grzeszczyk Barbara,
Furman Bartłomiej,
Chmielewski Marek
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400226
Subject(s) - chemistry , isocyanate , cycloaddition , diastereomer , polymer chemistry , stereoselectivity , intramolecular force , propenyl , polystyrene , dendrimer , polymer , organic chemistry , catalysis , polyurethane
Abstract 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)