Letter
Ir-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Alkylations
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Abstract

[Ir(COD)Cl]2/phosphoramidite ligand 1a was found to be an efficient catalytic system for the highly regio- and enantioselective decarboxylative alkylation of γ-substituted allyl β-ketocarboxylates, affording the branched products with up to >99/1 branched-linear ratio and 96% ee.
Citing Articles
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This article has been cited by 13 ACS Journal articles (5 most recent appear below).

Deacylative Allylation: Allylic Alkylation via Retro-Claisen Activation
Alexander J. Grenning and Jon A. TungeJournal of the American Chemical Society2011 133 (37), 14785-14794Deacylative Allylation: Allylic Alkylation via Retro-Claisen Activation
Alexander J. Grenning and Jon A. TungeJournal of the American Chemical Society2011 133 (37), 14785-14794A new method for allylic alkylation of a variety of relatively nonstabilized carbon nucleophiles is described herein. In this process of “deacylative allylation”, the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-...

Palladium-Catalyzed Decarboxylative Coupling of Potassium Nitrophenyl Acetates with Aryl Halides
Rui Shang, Zheng Huang, Ling Chu, Yao Fu, and Lei LiuOrganic Letters2011 13 (16), 4240-4243Palladium-Catalyzed Decarboxylative Coupling of Potassium Nitrophenyl Acetates with Aryl Halides
Rui Shang, Zheng Huang, Ling Chu, Yao Fu, and Lei LiuOrganic Letters2011 13 (16), 4240-4243A palladium-catalyzed decarboxylative cross-coupling of potassium 2- and 4-nitrophenyl acetates with aryl chlorides and bromides has been developed. Because the nitro group can be readily converted to many other functional groups, the new reaction ...

Carbon−Sulfur Bond Formation via Iridium-Catalyzed Asymmetric Allylation of Aliphatic Thiols
Ning Gao, Shengcai Zheng, Weikang Yang, and Xiaoming ZhaoOrganic Letters2011 13 (6), 1514-1516Carbon−Sulfur Bond Formation via Iridium-Catalyzed Asymmetric Allylation of Aliphatic Thiols
Ning Gao, Shengcai Zheng, Weikang Yang, and Xiaoming ZhaoOrganic Letters2011 13 (6), 1514-1516An iridium-catalyzed regio- and enatioselective allylation with aliphatic thiols as the nucleophile in dichloromethane has been accomplished; and the branch products were obtained in 34−80% yields with up to 94/6 b/l and 98% ee.

Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions
Jimmie D. Weaver, Antonio Recio, III, Alexander J. Grenning, and Jon A. TungeChemical Reviews2011 111 (3), 1846-1913Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions
Jimmie D. Weaver, Antonio Recio, III, Alexander J. Grenning, and Jon A. TungeChemical Reviews2011 111 (3), 1846-1913

Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution
John F. Hartwig and Levi M. StanleyAccounts of Chemical Research2010 43 (12), 1461-1475Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution
John F. Hartwig and Levi M. StanleyAccounts of Chemical Research2010 43 (12), 1461-1475Enantioselective allylic substitution reactions comprise some of the most versatile methods for preparing enantiomerically enriched materials. These reactions form products that contain multiple functionalities by creating carbon−nitrogen, carbon−oxygen,...
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History
- Published In Issue October 11, 2007
- Received August 9, 2007
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