345222-33-5Relevant academic research and scientific papers
A novel and simple method for the preparation of (R)- and (S)-pyrrolidine-2-phosphonic acids: Phosphonic acid analogues of proline
Kaboudin, Babak,Kato, Jun-Ya,Aoyama, Hiroshi,Yokomatsu, Tsutomu
, p. 1562 - 1566 (2013)
A simple and convenient method has been developed for the preparation of (R)- and (S)-pyrrolidine-2-phosphonic acids. The thermal reaction of proline with diethyl phosphite in the presence of benzaldehyde gave an N-benzyl derivative of diethyl pyrrolidine-2-phosphonate, which was transformed into two diastereomeric amides by sequential debenzylation and acylation with (+)-dibenzoyl-l-tartaric anhydride. The two diastereomeric amides were separated by column chromatography and the structure of one of them was determined by X-ray crystallographic analysis. Hydrolysis of the amides in the usual manner afforded (R)- and (S)-pyrrolidine-2-phosphonic acids. The advantages of the present method are that it is easy, rapid, and prepares both enantiomers of pyrrolidine-2-phosphonic acids.
A catalyst-free, three-component decarboxylative coupling of amino acids with aldehydes and H-dialkylphosphites for the synthesis of α- aminophosphonates
Kaboudin, Babak,Karami, Leila,Kato, Jun-Ya,Aoyama, Hiroshi,Yokomatsu, Tsutomu
supporting information, p. 4872 - 4875 (2013/09/02)
A simple, efficient, and new method is developed for the synthesis of α-aminophosphonates via a three-component, catalyst-free decarboxylative coupling of amino acids with aldehydes and H-dialkyl phosphite. Treatment of amino acids with aldehydes and diethyl phosphite in the absence of catalyst, base, and ligand give α-aminophosphonates in moderate to good yields. This method is simple, rapid, and high-yielding.
Cerium(IV) oxide as a neutral catalyst for aldehyde-induced decarboxylative coupling of l-proline with triethyl phosphite and nitromethane
Firouzabadi, Habib,Iranpoor, Nasser,Ghaderi, Arash,Ghavami, Maryam
, p. 5515 - 5518 (2012/11/07)
The application of cerium(IV) oxide (CeO2) as a neutral and heterogeneous catalyst for aldehyde-induced decarboxylative coupling of l-proline with triethyl phosphite and nitromethane is described. In addition, a [3+2] cycloaddition reaction of the in situ generated 1,3-dipolar intermediate with benzaldehyde in the absence of a nucleophile is also reported. 2012 Elsevier Ltd. All rights reserved.
Copper/DIPEA-catalyzed, aldehyde-induced tandem decarboxylation-coupling of natural α-amino acids and phosphites or secondary phosphine oxides
Yang, Dongxu,Zhao, Depeng,Mao, Lijuan,Wang, Linqing,Wang, Rui
experimental part, p. 6426 - 6431 (2011/09/15)
A copper/DIPEA-catalyzed, aldehyde-induced intermolecular decarboxylative coupling reaction of natural α-amino acids and phosphites or secondary phosphine oxides was developed. In this process, a series of potentially useful ligands for organic synthesis
