56475-88-8Relevant academic research and scientific papers
Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions
Aukland, Miles H.,Grossmann, Oleg,Lee, Sunggi,List, Benjamin,Maji, Rajat
supporting information, (2022/01/19)
Strong and confined imidodiphosphorimidate (IDPi) catalysts enable highly enantioselective substitutions of cyclic, aliphatic hemiaminal ethers with enol silanes. 2-Substituted pyrrolidines, piperidines, and azepanes are obtained with high enantioselectiv
Photochemical rearrangement of N-mesyloxylactams: Stereospecific formation of N-heterocycles
Drouin, Alexandre,Winter, Dana K.,Pichette, Simon,Aubert-Nicol, Samuel,Lessard, Jean,Spino, Claude
, p. 164 - 169 (2011/03/19)
N-Mesyloxylactams undergo an efficient ring-contraction to N-heterocycles of various ring sizes. Yields increase with the degree of substitution α to the carbonyl. The stereochemical information of a chiral migrating carbon is conserved making this reacti
One-pot conversion of proline derivatives into iodinated iminosugar-based nucleosides, useful precursors of highly functionalized nucleoside analogues
Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo
scheme or table, p. 6633 - 6642 (2011/02/25)
Readily available proline derivatives can be transformed in one step into β-iodinated iminosugar-based nucleosides, under very mild conditions. The method couples a tandem radical decarboxylation-oxidation-β-iodination to the addition of nitrogen bases. T
Electrochemical deallylation of α-allyl cyclic amines and synthesis of optically active quaternary cyclic amino acids
Kirira, Peter G.,Kuriyama, Masami,Onomura, Osamu
experimental part, p. 3970 - 3982 (2010/07/04)
Electrochemical oxidation of α-allylated and α-betizylated N-acylated cyclic amines by using a graphite anode easily affords the corresponding α-methoxylated products with up to 76% yield. Ease of oxidation was affected by the type of electrode, the size
Photochemical rearrangement of N -chlorolactams: A route to N -heterocycles through concerted ring contraction
Winter, Dana K.,Drouin, Alexandre,Lessard, Jean,Spino, Claude
supporting information; experimental part, p. 2610 - 2618 (2010/06/17)
We report a novel ring contraction allowing the direct conversion of N-chlorolactams to their corresponding ring-contraction N-heterocycles upon photolysis. Results show that the rearrangement occurs with a variety of N-chlorolactams and that the greater the substitution at the migrating carbon, the greater the yield of product. Importantly, stereochemistry at the migrating carbon is conserved in the product. Rearranged products were isolated as their methyl carbamates in yields varying from 17% to 58%, with the major side product being the recyclable parent lactam.
The Mannich-type reaction between N,O-acetals and carbon nucleophiles under solvent-free conditions
Matsumura, Yoshihiro,Ikeda, Takashi,Onomura, Osamu
, p. 113 - 117 (2007/10/03)
The Mannich-type reaction for 1-methoxycarbonyl- or 1-benzyloxy-carbonyl-2-methoxylpyrrolidine with carbon nucleophiles such as acetylacetone, methyl acetoacetate, dimethyl malonates, benzoylacetone, dibenzoylmethane, or cyclohexane-1, 3-dione proceeded b
Microflow electroorganic synthesis without supporting electrolyte
Horcajada, Roberto,Okajima, Masayuki,Suga, Seiji,Yoshida, Jun-Ichi
, p. 1303 - 1305 (2008/09/16)
Anodic methoxylation of several organic compounds has been successfully achieved in the absence of intentionally added supporting electrolyte using an electrochemical microflow system. The Royal Society of Chemistry 2005.
Tandem radical decarboxylation-oxidation of amino acids: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping
Boto, Alicia,Hernandez, Rosendo,Suarez, Ernesto
, p. 4930 - 4937 (2007/10/03)
A convenient methodology for the synthesis of 2-substituted pyrrolidines from α-amino acids is described. A number of cyclic and acyclic α-amino acid derivatives have been prepared in order to test the scope and diastereoselectivity of this method. These substrates were treated with iodosylbenzene or (diacetoxyiodo)benzene (DIB) and iodine in order to generate the corresponding carboxyl radical, which evolves by loss of carbon dioxide to produce a carbon radical which in turn undergoes oxidation to an N-acyliminium ion. This postulated intermediate could be trapped inter- or intramolecularly by oxygen, nitrogen and carbon nucleophiles. In the case of carbon nucleophiles, a Lewis acid is required for the concomitant carbon-carbon bond formation. High yields and modest diastereoselectivities were obtained. The present methodology was applied to the synthesis of ω-amino aldehydes or hemiaminals 8-14, 2-aminopyrrolidine derivative 15, aminolactone derivative 16, and azasugar analogues 17 and 18. When carbon nucleophiles were used, alkaloid precursors such as 2-allyl- or 2-alkylpyrrolidines 19-23 and 25 were obtained.
A convenient method for synthesis of optically active methylphenidate from N-methoxycarbonylpiperidine by utilizing electrochemical oxidation and Evans aldol-type reaction
Matsumura, Yoshihiro,Kanda, Yasuhisa,Shirai, Kimihiro,Onomura, Osamu,Maki, Toshihide
, p. 7411 - 7422 (2007/10/03)
A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding α-methoxylated carbamate utilizing electrochemical oxidation f
Oxidative decarboxylation of α-amino acids: A mild and efficient method for the generation of N-acyliminium ions
Boto, Alicia,Hernandez, Rosendo,Suarez, Ernesto
, p. 5945 - 5948 (2007/10/03)
The oxidative decarboxylation of α-amino acids using the system (diacetoxyiodo)benzene or iodosylbenzene and iodine proceeded smoothly at room temperature. The intermediacy of an N-acyliminium cation has been demonstrated through intermolecular and intram
