期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 32, 页码 10343-10346出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201805323
关键词
copper; cycloaddition; diazo compounds; sulfonium salts; ylides
资金
- National Science Foundation [CHE-1464690, CHE-1625963]
- National Institutes of Health [G12MD007591]
- National Institute of General Medical Sciences branch of the National Institutes of Health (MARC-U*STAR) [GM07717]
Enoldiazoimides, a new subclass of enoldiazo compounds, generate enol-substituted carbonyl ylides whose reactions with sulfur ylides enable an unprecedented formal [4+2] cycloaddition. The resulting multifunctionalized indolizidinones, which incorporate sulfur, are formed in good yields under mild reaction conditions. The uniqueness of this transformation stems from the role of the silyl-protected enol, since the corresponding acetyldiazoimide failed to provide any cross-products in metal-catalyzed reactions with sulfur ylides. This copper-catalyzed cycloaddition is initiated with the generation of enol-substituted carbonyl ylides and sulfur ylides from enoldiazoimides and sulfonium salts, respectively, and proceeds through stepwise six-membered ring formation, C-O and C-S bond cleavage, and silyl and acetyl group migration.
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