100609-39-0Relevant academic research and scientific papers
Electrochemical Oxidative Coupling between Benzylic C(sp3)-H and N-H of Secondary Amines: Rapid Synthesis of α-Amino α-Aryl Esters
Chauhan, Pankaj,Choudhary, Rahul,Kumar, Indresh,Nagare, Yadav Kacharu,Pawar, Amol Prakash,Shah, Imtiyaz Ahmad,Yadav, Jyothi
, p. 9682 - 9691 (2021/07/26)
An intermolecular electrochemical coupling between the benzylic C(sp3)-H bond and various secondary amines is reported. The electronic behavior of two electronically rich units viz the α-position of α-aryl acetates and amines was engineered electrochemically, thus facilitating their reactivity for the direct access of α-amino esters. A series of acyclic/cyclic secondary amines and α-aryl acetates were tested to furnish the corresponding α-amino esters with high yields (up to 92%) under mild conditions.
Tandem N, N-Dialkylation Reaction of N-Trimethylsilyl α-Iminoesters Utilizing an Umpolung Reaction and Characteristics of the Silyl Substituent: Synthesis of Pyrrolidine, Piperidine, and Iminodiacetate
Mizota, Isao,Tadano, Yurie,Nakamura, Yusuke,Haramiishi, Tomoki,Hotta, Miyuki,Shimizu, Makoto
, p. 2663 - 2667 (2019/04/30)
Umpolung reactions of N-trimethylsilyl α-iminoester with organometallics gave directly N-alkylaminoesters in high yields without the need for removing a protecting group at the nitrogen atom. Efficient syntheses of pyrrolidines, piperidines, and iminodiacetate derivatives were also developed via tandem N,N- or N,C-dialkylation reactions utilizing characteristics of the silyl substituent. Furthermore, under the influence of silica gel, the addition of an enolate to the imino nitrogen proceeded to give an iminodiacetate derivative.
A formal method for the de-N,N-dialkylation of Sommelet-Hauser rearrangement products
Tayama, Eiji,Sato, Ryota,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu
, p. 4710 - 4718 (2012/07/28)
Selective amine de-alkylation enables the conversion of Sommelet-Hauser rearrangement products into 2-aryl-2-bromoacetic acid derivatives. These compounds are valuable synthetic intermediates in the synthesis of α-aryl-α-amino or α-aryl-β-amino acid deriv
Diastereoselective Petasis Mannich reactions accelerated by hexafluoroisopropanol: A pyrrolidine-derived arylglycine synthesis
Nanda, Kausik K.,Trotter, B. Wesley
, p. 2025 - 2028 (2007/10/03)
A diastereoselective synthesis of pyrrolidine-derived arylglycines has been developed using the Petasis boronic acid Mannich reaction. High diastereoselectivities in the reactions of chiral amines, aryl boronic acids, and glyoxylic acid monohydrate have been demonstrated for the first time. Key to the implementation of this method is the discovery that hexafluoroisopropanol accelerates the Petasis process, reducing reaction times from multiple days to less than 24 h.
