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Primary Amides. A General Nitrogen Source for Catalytic Asymmetric Aminohydroxylation of Olefins
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Section:Abstract
N-Bromo,N-lithio salts of primary carboxamides have been shown to be efficient nitrogen sources for catalytic asymmetric aminohydroxylation of olefins, behaving much like the parent N-bromoacetamide in these reactions. α-Chloro-N-bromoacetamide is a particularly interesting nitrogen source, as it is functionalized for further reaction, including easy deprotection by treatment with thiourea.
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This article has been cited by 10 ACS Journal articles (5 most recent appear below).
Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction
Lawrence Harris, Simon P. H. Mee, Richard H. Furneaux, Graeme J. Gainsford, and Andreas LuxenburgerThe Journal of Organic Chemistry2011 76 (2), 358-372Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction
Lawrence Harris, Simon P. H. Mee, Richard H. Furneaux, Graeme J. Gainsford, and Andreas LuxenburgerThe Journal of Organic Chemistry2011 76 (2), 358-372Ethyl- (7), benzyl- (8), tert-butyl- (9), and fluorenylmethyl-4-chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric ...
Advancing the Mechanistic Understanding of an Enantioselective Palladium-Catalyzed Alkene Difunctionalization Reaction
Katrina H. Jensen, Jonathan D. Webb, and Matthew S. SigmanJournal of the American Chemical Society2010 132 (49), 17471-17482Advancing the Mechanistic Understanding of an Enantioselective Palladium-Catalyzed Alkene Difunctionalization Reaction
Katrina H. Jensen, Jonathan D. Webb, and Matthew S. SigmanJournal of the American Chemical Society2010 132 (49), 17471-17482The mechanism of an enantioselective palladium-catalyzed alkene difunctionalization reaction has been investigated. Kinetic analysis provides evidence of turnover-limiting attack of a proposed quinone methide intermediate with MeOH and suggests that ...
Tethered Aminohydroxylation (TA) Reaction of Amides
Timothy J. Donohoe, Cedric K. A. Callens and Amber L. ThompsonOrganic Letters2009 11 (11), 2305-2307Tethered Aminohydroxylation (TA) Reaction of Amides
Timothy J. Donohoe, Cedric K. A. Callens and Amber L. ThompsonOrganic Letters2009 11 (11), 2305-2307The first examples of amide-tethered aminohydroxylation reactions, catalyzed by osmium, showing that the use of N−O-based reoxidants are essential for success, are reported. The system that is described is compatible with a variety of different alkene ...
Synthesis of β-Amino-α-hydroxy Esters and β-Amino-α-azido Ester by Sharpless Asymmetric Aminohydroxylation, Byproducts Analysis
Zuosheng Liu, Nianchun Ma, Yanxing Jia, Michèle Bois-Choussy, Adriano Malabarba, and Jieping ZhuThe Journal of Organic Chemistry2005 70 (7), 2847-2850Synthesis of β-Amino-α-hydroxy Esters and β-Amino-α-azido Ester by Sharpless Asymmetric Aminohydroxylation, Byproducts Analysis
Zuosheng Liu, Nianchun Ma, Yanxing Jia, Michèle Bois-Choussy, Adriano Malabarba, and Jieping ZhuThe Journal of Organic Chemistry2005 70 (7), 2847-2850Synthesis of enantiomerically pure β-amino-α-hydroxy esters (1, 2) and β-amino-α-azido ester (3) using Sharpless AA as a key step is described. A hitherto unreported side reaction, the oxidation of the β-hydroxy-α-amino ester (5) into the α,α-di-tert-...
Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines
Jared W. Evans and Jonathan A. EllmanThe Journal of Organic Chemistry2003 68 (26), 9948-9957Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines
Jared W. Evans and Jonathan A. EllmanThe Journal of Organic Chemistry2003 68 (26), 9948-9957N-tert-Butanesulfinyl α-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the α-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-...
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- Published In Issue July 27, 2000
- Received April 19, 2000
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