Catalytic Enantioselective [3 + 2]-Cycloadditions of Diazoketone-Derived Aryl-Substituted Carbonyl Ylides
β Scribed by Hodgson, David M.; Glen, Rebecca; Grant, Guy H.; Redgrave, Alison J.
- Book ID
- 120485910
- Publisher
- American Chemical Society
- Year
- 2003
- Tongue
- English
- Weight
- 98 KB
- Volume
- 68
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition reactions of tert-butyl 2-diazo-3,6-dioxoheptanoate 7 with alkyne and strained alkene dipolarophiles to afford the corresponding cycloadducts with up to 92% ee are described.
Tailor-made" carbonyl ylides bearing only alkyl substituents or no substituents were efficiently generated from a-chloroalkyl a'-chloroalkyl ethers in the presence of samarium reagents. Using these novel and synthetically practical carbonyl ylides, optionally substituted and stereochemically defmed