128372-99-6Relevant academic research and scientific papers
Chemoenzymatic Synthesis of Substituted Azepanes by Sequential Biocatalytic Reduction and Organolithium-Mediated Rearrangement
Zawodny, Wojciech,Montgomery, Sarah L.,Marshall, James R.,Finnigan, James D.,Turner, Nicholas J.,Clayden, Jonathan
supporting information, p. 17872 - 17877 (2019/01/04)
Enantioenriched 2-aryl azepanes and 2-arylbenzazepines were generated biocatalytically by asymmetric reductive amination using imine reductases or by deracemization using monoamine oxidases. The amines were converted to the corresponding N′-aryl ureas, which rearranged on treatment with base with stereospecific transfer of the aryl substituent to the 2-position of the heterocycle via a configurationally stable benzyllithium intermediate. The products are previously inaccessible enantioenriched 2,2-disubstituted azepanes and benzazepines.
Enantioselective Direct Synthesis of Free Cyclic Amines via Intramolecular Reductive Amination
Zhang, Ying,Yan, Qiaozhi,Zi, Guofu,Hou, Guohua
supporting information, p. 4215 - 4218 (2017/08/23)
Chiral cyclic amines can be prepared via intramolecular reductive amination of N-Boc-protected amino ketones in a one-pot process. With the complex of iridium and f-spiroPhos as the catalyst, a range of N-Boc-protected amino ketones are smoothly transformed into chiral cyclic free amines in high yields and excellent enantioselectivities (up to 97% ee). Moreover, this method can also be successfully applied to the synthesis of a κ-opioid receptor selective antagonist, (S)-1.
A One-Pot Process for the Enantioselective Synthesis of Amines via Reductive Amination under Transfer Hydrogenation Conditions
Williams, Glynn D.,Pike, Richard A.,Wade, Charles E.,Wills, Martin
, p. 4227 - 4230 (2007/10/03)
(Equation presented) Cyclic amines may be prepared via a sequence of deprotection followed by intramolecular reductive amination of t-Boc-protected amino ketones under asymmetric transfer hydrogenation conditions. In cases where the corresponding imine reaction proceeds with high enantioselectivity, this is reflected in the one-step process.
