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Full Paper
Titanocene(II)-Promoted Multicomponent Reactions Utilizing Alkynyl Sulfones, Alkenyl Sulfones, and Carbonyl Compounds: A Novel Method for the Synthesis of Vinylallenes
Article first published online: 30 OCT 2006
DOI: 10.1002/chem.200601326
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Ogata, A., Nemoto, M., Kobayashi, K., Tsubouchi, A. and Takeda, T. (2007), Titanocene(II)-Promoted Multicomponent Reactions Utilizing Alkynyl Sulfones, Alkenyl Sulfones, and Carbonyl Compounds: A Novel Method for the Synthesis of Vinylallenes. Chemistry - A European Journal, 13: 1320–1325. doi: 10.1002/chem.200601326
Publication History
- Issue published online: 9 JAN 2007
- Article first published online: 30 OCT 2006
- Manuscript Received: 15 SEP 2006
Funded by
- Grant-in-Aid for Scientific Research. Grant Number: 18 350 018
- Grant-in-Aid for Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resources”. Grant Number: 18 037 017
- Ministry of Education, Culture, Sports, Science and Technology (Japan)
- Abstract
- Article
- References
- Cited By
Keywords:
- allenes;
- cross-coupling;
- ketones;
- multicomponent reactions;
- olefination
Graphical Abstract
Cross-coupling: Titanocene(II)-promoted cross-coupling of alkynyl- and (Z)-alkenyl sulfones affords titanium vinylvinylidene complexes, which react with carbonyl compounds in a one-pot reaction to produce substituted vinylallenes with complete stereoselectivity (see scheme).
Abstract
Titanocene(II)-promoted cross coupling of alkynyl- and (Z)-alkenyl sulfones affords α-(phenylsulfonyl)alkenyltitanium species. Further treatment of these species with the titanocene(II) reagent generates titanium vinylvinylidene complexes, which react with carbonyl compounds in one pot to produce substituted vinylallenes with complete stereoselectivity. By using α,β-unsaturated ketones, 1,3,4,6-tetraenes are also obtained stereoselectively.