281664-24-2Relevant academic research and scientific papers
1,1′-Binaphthyldiamine-based lewis bases as readily available and efficient grganocatalysts for the reduction of N-Aryl and N-Alkyl ketimines
Guizzett, Stefania,Benaglia, Maurizio,Celentano, Giuseppe
experimental part, p. 3683 - 3687 (2009/12/03)
The development of simple, low-cost, efficient, and sustainable routes to enantiomerically pure amines is a topic of extraordinary interest, specially in view of future industrial applications. In this context, we wish to report a chemical and stereochemical efficient synthesis of chiral amines through the Lewis base activated trichlorosilane reduction of ketimines. An organocatalyst, easily prepared in a single step through the condensation of picolinic acid and commercially available 1,1′-binaphthyldiamine, is the key element of this metal-free methodology, that allowed the synthesis of chiral secondary and primary amines in high yields and stereose-lectivity. Noteworthy, such catalysts are able to promote the reduction of N-alkyl ketimines, often in quantitative yield and up to 87% enantioselectivity; it: is worth mentioning that for such transformations only one other organocatalytic system has been reported so far.
A chiral, oxidatively cleavable auxiliary in conjugate additions of lithium amides. Preparation of enantiomerically pure β-amino acid derivatives
Podlech, Joachim
, p. 1779 - 1786 (2007/10/03)
Addition of enantiomerically, pure 4-methoxyphanethyl-substituted lithium amides to α,β-unsaturated esters leads to β-amino acid derivatives 4 - 7 with selectivities > 95: 5. The auxiliary can be cleaved by oxidation with cerium(IV) ammonium nitrate (CAN) and subsequent hydrolysis of the resulting mixture of imines.
