161643-01-2Relevant articles and documents
A general study of aryloxo and alkoxo ligands in the titanium-catalyzed intermolecular hydroamination of terminal alkynes
Tillack, Annegret,Khedkar, Vivek,Jiao, Haijun,Beller, Matthias
, p. 5001 - 5012 (2005)
A general study of the regioselective hydroamination of terminal alkynes in the presence of Ti(NEt2)4 and different aryloxo and alkoxo ligands is presented. Depending on the ligand the regioselectivity towards the Markovnikov and the anti-Markovnikov addition product can be controlled. The experimentally observed isomer distribution is explained perfectly by detailed theoretical investigations which demonstrate that the regioselectivity is determined by the relative stability of the corresponding alkynetitanium π complexes. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Aliphatic and Aromatic Terminal Alkynes with Aliphatic Primary Amines
Kakiuchi, Fumitoshi,Kochi, Takuya,Morimoto, Yoshihiko
, p. 13143 - 13152 (2021/09/28)
Anti-Markovnikov hydroamination of both aliphatic and aromatic terminal alkynes with primary amines was achieved using an 8-quinolinolato rhodium catalyst to form aldimines and enamines in high yields. This catalytic system realized high functional group tolerance including hydroxy, bromo, cyano, and thioester groups.
Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades
Ramsden, Jeremy I.,Heath, Rachel S.,Derrington, Sasha R.,Montgomery, Sarah L.,Mangas-Sanchez, Juan,Mulholland, Keith R.,Turner, Nicholas J.
, p. 1201 - 1206 (2019/01/21)
The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.