Cyclic Sulfonamides via the Ring-Closing Metathesis Reaction. -Ring closing metathesis of various allyl-and vinylsulfonylamides in the presence of Grubb's ruthenium catalyst yields novel cyclic allyl-and vinylsultams. In the case of substrate (IX), the pyrrole (X) is formed instead of the expected
Cyclic sulfonamides via the ring-closing metathesis reaction
β Scribed by Paul R. Hanson; Donald A. Probst; Randall E. Robinson; Mei Yau
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 244 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The first examples of ring-closing metathesis (RCM) reactions on allyl-and vinylsulfonamide templates 1 and 2 catalyzed by the Grubbs ruthenium alkylidene 3 are described. The rate of cyclization of these reactions are sensitive to simple olefin substitution. These RCM reactions yield novel cyclic allyl-and vinylsultams 4 and 5 and represent our initial efforts toward the construction of novel sulfonamides.
π SIMILAR VOLUMES
Ring-closing olefin metathesis using the Grubbs catalyst was applied to the cyclisative release of resin-bound sulfonamides. Flexible linkers apparently facilitated the cyclisation-cleavage, allowing a number of novel cyclic sulfonamides to be prepared in good yields using catalytic amounts of the G