Disulfonimide‐Catalyzed Asymmetric Reduction of
<i>N</i>
‐Alkyl Imines
作者:Vijay N. Wakchaure、Philip S. J. Kaib、Markus Leutzsch、Benjamin List
DOI:10.1002/anie.201504052
日期:2015.9.28
A chiral disulfonimide (DSI)‐catalyzedasymmetric reduction of N‐alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O has been developed. The reaction delivers Boc‐protectedN‐alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross‐coupling of ketones with diverse
Enantioselective reduction of <i>N</i>-alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions
作者:Dan M. Mercea、Michael G. Howlett、Adam D. Piascik、Daniel J. Scott、Alan Steven、Andrew E. Ashley、Matthew J. Fuchter
DOI:10.1039/c9cc02900a
日期:——
Enantioselective reduction of ketimines was demonstrated using chiral N-heterocyclic carbene (NHC)-stabilised borenium ions in frustratedLewispair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N-alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step
METHOD FOR PRODUCING OPTICALLY ACTIVE AMINE COMPOUND
申请人:Kanto Kagaku Kabushiki Kaisha
公开号:US20130197234A1
公开(公告)日:2013-08-01
The present invention relates to methods for producing an optically active amine compound via a highly enantioselective hydrogenation reaction of an imine compound, wherein the imine compound is hydrogenated using a ruthenium metal complex having high catalytic activity and represented by Formula (1)
RuXYAB (1)
such as RuBr
2
[(S,S)-xylskewphos][(S,S)-dpen].
In the presence of an iridium compound, an imine of the following formula (1):
wherein R1, R2 and R3 are each, identical to or different from one another, a hydrogen atom or a non-reactive organic group, where R1 and R2 may be combined to form a ring together with the adjacent carbon atom, is reacted with a diazoacetic acid derivative of the following formula (2):
N2CHR4 (2)
wherein R4 is a cyano group, an alkoxycarbonyl group, a carbamoyl group or the like, to yield an aziridine compound of the following formula (5):
wherein R1, R2, R3 and R4 have the same meanings as defined above. The process can easily and efficiently produce aziridine compounds.
Method of producing an optically active amine compound by catalytic asymmetric hydrogenation using a ruthenium-diphosphine complex
申请人:Kanto Kagaku Kabushiki Kaisha
公开号:EP2623509A1
公开(公告)日:2013-08-07
The present invention relates to a method for hydrogenating an imine to an optically active amine using a ruthenium metal complex represented by Formula (1)
RuXYAB (1)
such as RuBr2[(S,S )-xylskewphos][(S,S )-dpen];
A is defined as a diphosphine compound represented by Formula (2),
B is defined as a diamine compound represented by Formula (3)
本发明涉及一种使用由式(1)表示的钌金属配合物将亚胺氢化为光学活性胺的方法
RuXYAB (1)
如 RuBr2[(S,S )-xylskewphos] [(S,S)-dpen];
A 定义为由式(2)表示的二膦化合物、
B 定义为由式(3)表示的二胺化合物