1163726-12-2Relevant articles and documents
A highly efficient synthesis of optically active ferrocenylethylamines via hydride reduction of chiral ferrocenylketimines
Qian, Hengyu,Yan, Shihai,Cui, Xiuling,Pi, Chao,Liu, Cheng,Wu, Yangjie
, p. 992 - 996 (2013/09/02)
Due to using (R)- or (S)-α-methylbenzylamine as a chiral auxiliary, and low-temperature regime for reduction of the intermediate ferrocenyl-mono- or 1,1′-bis-ketimines, the corresponding secondary mono- or 1,1′-bis-amines were prepared with high diastereoselectivity. Removal of the α-methylbenzyl group afforded the optically active primary mono- and bis-ferrocenylethylamines in high yields. The absolute configuration of (R,R)-3a and (S,S)-3b was determined by X-ray single crystal diffraction. We have developed an efficient and highly stereoselective synthesis of the chiral mono- and bis-ferrocenylamines via sodium borohydride reduction, followed by reductive cleavage of the α-methylbenzyl moiety using 5% Pd/C and HCOONH 4. The selectivity was up to 99% de. Copyright
A convenient, highly stereoselective, metal-free synthesis of chiral amines
Guizzetti, Stefania,Benaglia, Maurizio,Biaggi, Cinzia,Celentano, Giuseppe
supporting information; experimental part, p. 134 - 136 (2010/07/16)
A low cost, efficient, metal-free highly stereoselective reduction of ketimines to chiral amines was developed. Different imines bearing a very cheap and removable chiral auxiliary were reduced simply by trichlorosilane in the presence of N,N-dimethylformamide, often in quantitative yield and complete control of the absolute stereochemistry, to afford highly enantiomerically enriched amines. Georg Thieme Verlag Stuttgart.
Highly stereoselective metal-free catalytic reduction of Lmines: An easy entry to enantiomerically pure amines and natural And Unnatural α-amino esters
Gulzzettl, Stefania,Benagila, Maurizio,Rossi, Sergio
supporting information; scheme or table, p. 2928 - 2931 (2009/12/05)
A highly efficient catalytic stereoselective ketlmlne reduction is described. The combination of an Inexpensive chiral organocatalyst, easily prepared In a single step, and of a very cheap removable chiral auxiliary allowed us to obtain enantlomerlcally pure amino compounds. The methodology allowed synthesis of chiral secondary and primary amines and natural and unnatural amino esters In high yields often with total control of the absolute stereochemistry.
