- Nucleophilic substitution of (alkoxymethylene)dimethylammonium chloride with potassium phthalimide; a convenient procedure for the synthesis of imides with inversion of configuration
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Secondary alcohols are converted into their phthalimido derivatives with inversion of configuration via sequential reaction with (chloromethylene)dimethylammonium chloride and potassium phthalimide.
- Barrett, Anthony G. M.,Braddock, D. Christopher,James, Rachel A.,Procopiou, Panayiotis A.
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- Amplification of the chiroptical response of UV-Transparent amines and alcohols by: N-phthalimide derivatization enabling absolute configuration determination through ECD computational analysis
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The stereoselective transformation of chiral UV-Transparent amines and alcohols to phthalimides has proved to be a simple and efficient method to enhance the chiroptical response of these substrates allowing their reliable absolute configuration determination by computational analysis of ECD spectra. Such a transformation also leads to a significant reduction in the molecular conformational flexibility thus simplifying the conformational analysis required by the computational treatment. The method described herein thus allows the absolute configuration assignment to these challenging substrates to be much easier and reliable.
- Belviso, Sandra,Mazzeo, Giuseppe,Padula, Daniele,Santoro, Ernesto,Scafato, Patrizia,Superchi, Stefano
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p. 2094 - 2102
(2020/03/27)
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- Synthesis and evaluation of some variants of the Nefkens' reagent
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A series of N-substituted phthalimides have been prepared in an effort to explore synthetic variants of the Nefkens' reagent. Three N-acylphthalimides [R = -CH3, -CH2CH3, and -C(CH3) 3] were prepared and employed for the protection of a series of representative amines. In addition, an N-methanesulfonylphthalimide and N-(diethylphosphoryl)phthalimide were also prepared. It was determined that among the phthalimides that were prepared N-propanoylphthalimide was the most effective reagent for the protection reaction.
- Goodman, Cassie A.,Hamaker, Christopher G.,Hitchcock, Shawn R.
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supporting information
p. 6012 - 6014
(2013/10/22)
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- 2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF
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An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.
- Pace, Vittorio,Hoyos, Pilar,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
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supporting information; experimental part
p. 1380 - 1382
(2010/09/05)
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- Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride
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The use of imidate esters as potential replacements for diethyl azodicarboxylate and triphenylphosphine in the Mitsunobu reaction is described. A series of secondary alcohols were allowed to react with (chloromethylene)dimethylammonium chloride, generated from dimethylformamide (DMF) and oxalyl chloride, to give imidate esters. Reaction of these salts with potassium benzoate or potassium phthalimide gave the products of SN2 substitution in excellent yields with clean inversion of stereochemistry. Optimization of reaction conditions is discussed as a means to increase the atom economy of the process by minimizing the quantity of nucleophile required.
- Barrett, Anthony G. M.,Braddock, D. Christopher,James, Rachel A.,Koike, Nobuyuki,Procopiou, Panayiotis A.
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p. 6273 - 6280
(2007/10/03)
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- Preparation of Optically Active Amines by a Combination of Gabriel Synthesis and Optical Resolution. X-Ray Crystal Structure of the Adduct between (-)-10,10'-Dihydroxy-9,9'-biphenanthryl and N-(1-tert-Butyl-2-oxoazetidin-3-yl)phthalimide
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Phthalimides which have a chiral alkyl group on the nitrogen atom, and which can easily be derived from potassium phthalimide and a chiral alkyl halide, were resolved by complexation with an optically active host compound.Decomposition, with hydrazine, of the resolved phthalimides gave optically active amines.Chiral recognition in an inclusion crystal of optically active N-azetidinone-substituted phthalimide and the optically active 10,10'-dihydroxy-9,9'-biphenanthryl host compound was studied by X-ray structure analysis.
- Toda, Fumio,Soda, Shinichi,Goldberg, Israel
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p. 2357 - 2362
(2007/10/02)
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- N-Alkylation of Imides with O-Alkylisourea under Neutral Conditions
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N-Alkylation of imides with O-alkylisoureas has been found to accur under neutral conditions.Stereochemical data and structural factors indicate that an SN2 mechanism is operative.
- Inoue, Yoshio,Taguchi, Masaaki,Hashimoto, Harukichi
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p. 332 - 334
(2007/10/02)
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- Synthesis of (R)- and (S)-2-Aminobutane from (S)- and (R)-2-Aminobutanol
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(R)-(-)- and (S)-(+)-2-Aminobutane (1) can be synthesized in good yield and high optical purity from (S)-(+)- and (R)-(-)-2-aminobutanol (2) respectively.
- Santaniello, Enzo,Casati, Rosangela,Milani, Fulvia
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p. 919 - 922
(2007/10/02)
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