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Catalytic Asymmetric Hiyama Cross-Couplings of Racemic α-Bromo Esters
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Abstract
The first catalytic asymmetric cross-coupling of α-halo carbonyl compounds with aryl metal reagents has been developed, thereby generating synthetically useful α-aryl carboxylic acid derivatives in good enantiomeric excess. The method can also be applied to enantioselective alkenylation reactions.
Citing Articles
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This article has been cited by 28 ACS Journal articles (5 most recent appear below).
Synthesis of α,α-Disubstituted α-Amino Esters: Nucleophilic Addition to Iminium Salts Generated from Amino Ketene Silyl Acetals
Shingo Hata, Hiroshi Koyama, and Makoto ShimizuThe Journal of Organic Chemistry2011 76 (23), 9670-9677Synthesis of α,α-Disubstituted α-Amino Esters: Nucleophilic Addition to Iminium Salts Generated from Amino Ketene Silyl Acetals
Shingo Hata, Hiroshi Koyama, and Makoto ShimizuThe Journal of Organic Chemistry2011 76 (23), 9670-9677Alkoxycarbonyl iminium species are prepared easily by the oxidation of tetrasubstituted amino ketene silyl acetals, and subsequent nucleophilic addition of Grignard reagents to the iminium salts gives α,α-disubstituted α-amino ester derivatives in ...
Pd/Josiphos-Catalyzed Enantioselective α-Arylation of Silyl Ketene Acetals and Mechanistic Studies on Transmetalation and Enantioselection
Kenya Kobayashi, Yasunori Yamamoto, and Norio MiyauraOrganometallics2011 30 (22), 6323-6327Pd/Josiphos-Catalyzed Enantioselective α-Arylation of Silyl Ketene Acetals and Mechanistic Studies on Transmetalation and Enantioselection
Kenya Kobayashi, Yasunori Yamamoto, and Norio MiyauraOrganometallics2011 30 (22), 6323-6327Palladium/(4-MeO-3,5-MePh)2PF-Pcy2) catalyzed the enantioselective arylation of silyl ketene acetals with iodoarenes in the presence of TlOAc to promote transmetalation of silyl ketene acetals. The highest enantioselectivities giving α-arylesters up to 91%...
Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature
Christophe Duplais, Arkady Krasovskiy, and Bruce H. LipshutzOrganometallics2011 30 (22), 6090-6097Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature
Christophe Duplais, Arkady Krasovskiy, and Bruce H. LipshutzOrganometallics2011 30 (22), 6090-6097Negishi-like cross-couplings between (functionalized) alkyl and aryl bromides are described. Despite the fact that organozinc reagents are intolerant of water, their formation as well as their use in an aqueous micellar environment is discussed herein. ...
Nickel-Catalyzed Asymmetric α-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and Room-Temperature Reactions
Shaozhong Ge and John F. HartwigJournal of the American Chemical Society2011 133 (41), 16330-16333Nickel-Catalyzed Asymmetric α-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and Room-Temperature Reactions
Shaozhong Ge and John F. HartwigJournal of the American Chemical Society2011 133 (41), 16330-16333We report the α-arylation of ketones with a range of aryl chlorides with enantioselectivities from 90 to 99% ee catalyzed by the combination of Ni(COD)2 and (R)-BINAP and the coupling of ketones with a range of heteroaryl chlorides with ...
An Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters
Zhiyan Huang, Zheng Liu, and Jianrong (Steve) ZhouJournal of the American Chemical Society2011 133 (40), 15882-15885An Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters
Zhiyan Huang, Zheng Liu, and Jianrong (Steve) ZhouJournal of the American Chemical Society2011 133 (40), 15882-15885In transition-metal catalyzed, asymmetric α-arylation of carbonyl compounds, formation of tertiary centers with high enantioselectivity is a longstanding problem, due to easy enolization of the monoarylation products. Herein, we report such examples using ...
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History
- Published In Issue March 19, 2008
- Received February 6, 2008
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