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Solid‐Phase [2+2] Cycloadditions between Chlorosulfonyl Isocyanate and Chiral Vinyl Ethers
Author(s) -
Łysek Robert,
Furman Bartłomiej,
Cierpucha Maciej,
Grzeszczyk Barbara,
Matyjasek Łukasz,
Chmielewski Marek
Publication year - 2002
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 - 10.1002/1099-0690(200207)2002:14<2377::aid-ejoc2377>3.0.co;2-i
Subject(s) - chemistry , isocyanate , oxetane , diastereomer , polymer chemistry , vinyl polymer , organic chemistry , intramolecular force , polymer , polymerization , polyurethane
Vinyl ethers 10 , 23 , and 33 were attached to Wang resin through the p ‐oxyphenylsulfonyl linker. The [2+2] cycloadditions between chlorosulfonyl isocyanate and the polymer‐bound vinyl ethers 12 , 24 , and 34 , followed by intramolecular alkylation of the β‐lactam nitrogen atom, gave mixtures of the corresponding diastereomeric clavams 8 / 9 and 21 / 22 or the oxacephams 31 / 32 , accompanied by the oxirane 7 or the oxetane 30 , respectively. This cyclization/cleavage step was performed in the presence of the strong organic bases BEMP and DBU. The corresponding reaction sequences performed in solution provided the oxabicyclic β‐lactams without the accompanying anhydrosugars. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)