281681-23-0Relevant articles and documents
C-H Amination via Electrophotocatalytic Ritter-Type Reaction
Lambert, Tristan H.,Shen, Tao
supporting information, p. 8597 - 8602 (2021/06/28)
A method for C-H bond amination via an electrophotocatalytic Ritter-Type reaction is described. The reaction is catalyzed by a trisaminocyclopropenium (TAC) ion in an electrochemical cell under irradiation. These conditions convert benzylic C-H bonds to acetamides without the use of a stoichiometric chemical oxidant. A range of functionality is shown to be compatible with this transformation, and several complex substrates are demonstrated.
Lipase-catalyzed resolution of chiral 1,3-amino alcohols: application in the asymmetric synthesis of (S)-dapoxetine
Torre, Oliver,Gotor-Fernandez, Vicente,Gotor, Vicente
, p. 860 - 866 (2007/10/03)
The enzymatic resolution of 3-amino-3-phenylpropan-1-ol derivatives has been studied through acylation processes. Candida antarctica lipase A (CAL-A) has been identified as the best biocatalyst for the transesterification reaction of 3-amino-3-phenyl-1-tert-butyldimethylsilyloxy-propan-1-ol using ethyl methoxyacetate as acylating agent and tert-butyl methyl ether as solvent. This enzymatic study has allowed us to obtain a valuable intermediate for the production of (S)-dapoxetine, which has been synthesized in good overall yield and high enantiomeric excess.
A convenient synthesis of dihydro- and tetrahydro-1,3-thiazine derivatives from β-aryl-β-amino acids
Leflemme, Nicolas,Dallemagne, Patrick,Rault, Sylvain
, p. 1503 - 1505 (2007/10/03)
A facile synthesis of 2-alkyl-4-aryl-5,6-dihydro-4H-1,3-thiazines and cis-2-alkyl-4-aryl-3,4,5,6-tetrahydro-2H-1,3-thiazines with potential therapeutic interest was achieved starting from readily accessible β-aryl-β-amino acids.
'Transmitted' remote double diastereoselection effects on the asymmetric reduction of β-boronate oxime ethers
Sailes, Helen E.,Watts, John P.,Whiting, Andrew
, p. 2457 - 2461 (2007/10/03)
Remote asymmetric induction in the reduction of a homochiral β-boronate oxime ether to the corresponding amine failed to provide asymmetric induction with a chiral reducing agents, but use of a chiral reducing agent produced extreme double diastereoselection effects which show that remote asymmetry can be 'transmitted' by suitable choice of a 'partner' molecule. (C) 2000 Published by Elsevier Science Ltd.
Studies on the asymmetric reduction of β-oximino methyl ether boronates: Reagent control, double diastereocontrol and transmitted remote asymmetric induction
Sailes, Helen E.,Watts, John P.,Whiting, Andrew
, p. 3362 - 3374 (2007/10/03)
High asymmetric induction (94% ee) could be obtained in the reduction of the achiral E-oxime ether boronate 5 with a homochiral oxazaborolidine 13-BH3-THF complex. Application of this homochiral reducing agent system to non-aromatic oxime ethers 21 produced low to moderate asymmetric induction. Application of the same homochiral reducing agent system to reduction of homochiral boronate E-oximes 3 and 4 produced extreme double diastereo-selection effects, i.e. 8 and 95% ee respectively, which demonstrated that remote asymmetry was being 'transmitted' by a suitable choice of a 'partner' molecule from the boronate moiety to the oxime during reduction. However, attempts to obtain direct remote asymmetric induction in the reduction of homochiral β-oximino boronate methyl ethers 3 and 4 to the corresponding amines produced zero, with for example BH3-THF complex, up to 28% ee with an Et3N-BH3-THF mixture (after oxidative boronate ester cleavage).
