RESIN-IMMOBILIZED BENZYL AND ARYL VINYL SULFONES - NEW VERSATILE TRACELESS LINKERS FOR SOLID-PHASE ORGANIC-SYNTHESIS

Authors
KROLL FEK MORPHY R REES D GANI D
Citation
Fek. Kroll et al., RESIN-IMMOBILIZED BENZYL AND ARYL VINYL SULFONES - NEW VERSATILE TRACELESS LINKERS FOR SOLID-PHASE ORGANIC-SYNTHESIS, Tetrahedron letters, 38(49), 1997, pp. 8573-8576
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
49
Year of publication
1997
Pages
8573 - 8576
Database
ISI
SICI code
0040-4039(1997)38:49<8573:RBAAVS>2.0.ZU;2-P
Abstract
New polystyrene-based resins containing benzyl and aryl vinyl sulfone groups are described. The vinyl sulfone group reacts efficiently with 2 degrees amines, via conjugate addition, and the resin-bound 3 degree s amine products can be quaternised through alkylation. Subsequent dea mination to give 3 degrees amines and the regenerated vinyl sulfone oc curs in moderate to good yield. Both systems can be recycled and show moderate stability to acids and high stability to nucleophiles includi ng Grignard reagents. (C) 1997 Elsevier Science Ltd.