58917-85-4Relevant articles and documents
A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf
, p. 10456 - 10460 (2015/11/10)
N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.
Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction
Harris, Lawrence,Mee, Simon P. H.,Furneaux, Richard H.,Gainsford, Graeme J.,Luxenburger, Andreas
, p. 358 - 372 (2011/04/17)
Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.
Resolution of N-Protected amino alcohols by porcine pancreatic lipase
Magrioti, Victoria,Fotakopoulou, Irene,Athinaios, Nicolaos,Anastasopoulou, Panoula,Constantinou-Kokotou, Violetta,Kokotos, George
scheme or table, p. 159 - 162 (2010/08/19)
The resolution of 2-amino alcohols protected by urethane-type groups either via porcine pancreatic lipase (PPL) hydrolysis of the corresponding racemic acetates or via PPL catalyzed transesterification of racemic alcohols was studied. In both cases, Boc protecting group led to better chemical yields and enantiopurities than Z and Fmoc protecting groups. Furthermore, a simple and efficient method for the synthesis of the medicinally interesting optically pure (R)-2- aminohexadecanol was developed.