25102-89-0Relevant articles and documents
PROCESS FOR PREPARING AMINE COMPOUND
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Page/Page column 13, (2012/03/27)
The present invention aims to provide a practical process for preparing amine compounds through a generalized highly-diastereoselective reductive amination reaction. The present invention relates to a process for diastereoselectively preparing an amine co
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.
Ytterbium acetate promoted asymmetric reductive amination: Significantly enhanced stereoselectivity
Nugent, Thomas C.,El-Shazly, Mohamed,Wakchaure, Vijay N.
, p. 1297 - 1305 (2008/09/17)
(Chemical Equation Presented) Reductive amination of prochiral unhindered 2-alkanones 1 with (R)- or (S)-α-MBA in the presence of Yb(OAc) 3 (50-110 mol %), Raney-Ni, and hydrogen (120 psi) results in increased diastereoselectivity for the amine products 2 (80-89% de) with good yield (80-87%). The increased de is based on comparison with the best previously reported de's when using (R)- or (S)-α-MBA, regardless of the strategy employed [stepwise (isolation of ketimines) or one-pot (reductive amination)], reducing agent examined, or achiral Lewis acid or Bronsted acid examined. An in situ cis- to trans-ketimine isomerization mechanism, promoted by Yb(OAc)3, has been proposed to account for the observed increase in diastereoselectivity and suggests a new entry into the control of ketimine geometry.