PALLADIUM(0)-CATALYZED ALLYLATION OF HIGHLY ACIDIC AND NON-NUCLEOPHILIC ARENESULFONAMIDES, SULFAMIDE, AND CYANAMIDE - I

Authors
CEREZO S CORTES J MORENOMANAS M PLEIXATS R ROGLANS A
Citation
S. Cerezo et al., PALLADIUM(0)-CATALYZED ALLYLATION OF HIGHLY ACIDIC AND NON-NUCLEOPHILIC ARENESULFONAMIDES, SULFAMIDE, AND CYANAMIDE - I, Tetrahedron, 54(49), 1998, pp. 14869-14884
Citations number
74
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
49
Year of publication
1998
Pages
14869 - 14884
Database
ISI
SICI code
0040-4020(1998)54:49<14869:PAOHAA>2.0.ZU;2-3
Abstract
Arenesulfonamides, sulfamide, and cyanamide are efficiently allylated using allylic carbonates under Pd(0)catalysis. N-Arenesulfonyl-2,5-dih ydropyrroles are obtained by ruthenium-mediated ring closing metathesi s of the corresponding N-diallylated compounds. A stereochemical study of the reactions of ethyl cis-(5-methyl-2-cyclohexenyl) carbonate wit h 2,4,6-triisopropylphenylsulfonamide was performed, clean overall ret ention of configuration being found with bidentate phosphines. (C) 199 8 Elsevier Science Ltd. All rights reserved.