Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5217821 | Tetrahedron | 2013 | 7 Pages |
Abstract
Five- and seven-membered sultam derivatives were conveniently synthesized via intra- or intermolecular Michael additions and an improved vinyl sulfonamide Baylis-Hillman reaction. Two different cyclization pathways were explored for the oxa-Michael reaction. A good solvent was discovered for an otherwise sluggish ketone-type Baylis-Hillman reaction in which vinyl sulfonamide ketones were used as the precursors. Furthermore, a strong base caused vinyl sulfonamide ketones to undergo 5-endo-trig intramolecular cyclizations, which are disfavored according to Baldwin's rule. Finally Baylis-Hillman reaction products were used as scaffolds for diversity-oriented sultam syntheses.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Kun Tong, Jinchang Tu, Xueyong Qi, Min Wang, Yanjie Wang, Haizhen Fu, Charles U. Jr., Aihua Zhou,