109774-57-4Relevant articles and documents
Direct stereospecific amination of alkyl and aryl pinacol boronates
Mlynarski, Scott N.,Karns, Alexander S.,Morken, James P.
, p. 16449 - 16451,3 (2020/09/15)
The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.
A convenient synthesis of N-Boc-protected tert-butyl esters of phenylglycines from benzylamines
Kise, Naoki,Ozaki, Hiroshi,Terui, Hiroaki,Ohya, Kengo,Ueda, Nasuo
, p. 7637 - 7639 (2007/10/03)
The N,N-di-Boc-protected benzylamines undergo [1,2] Boc migration on treatment with KDA/t-BuOLi. By this reaction, the corresponding N-Boc-protected t-butyl esters of phenylglycines are obtained in high yields.
A Simple Method for tert-Butoxycarbonylation of Amides
Grehn, Leif,Gunnarsson, Kerstin,Ragnarsson, Ulf
, p. 745 - 750 (2007/10/02)
The tert-butoxycarbonyl (Boc) function was conveniently introduced onto the amide nitrogen in several secondary amides using di-tert-butyl dicarbonate in dry acetonitrile with 4-dimethylaminopyridine as catalyst.Carboxamides with different acyl groups such as formyl, acetyl and benzoyl are presented as well as derivatives of carbamic acid.Examples also include other amide types: sulfonamide, sulfenamide and phosphinamide which were all smoothly converted to the corresponding Boc derivatives under these conditions.The yields were generally excellent and the resulting Boc analogues stable compounds which could be stored for months under ordinary conditions.Some stereochemical and structural aspects of this acylation are also discussed.Bulky substituents in the proximity of the amide moiety significantly retarded the reaction and in some cases no product was detected.For one compound with an activated methine group, C acylation was observed.
