Stereoelectronic Basis for the Kinetic Resolution of N-Heterocycles with Chiral Acylating Reagents
نویسندگان
چکیده
منابع مشابه
Catalytic Kinetic Resolution of Saturated N-Heterocycles by Enantioselective Amidation with Chiral Hydroxamic Acids.
The preparation of enantioenriched chiral compounds by kinetic resolution dates back to the laboratories of Louis Pasteur in the middle of the 19th century. Unlike asymmetric synthesis, this process can always deliver enantiopure material (ee > 99%) if the reactions are allowed to proceed to sufficient conversion and the selectivity of the process is not unity (s > 1). One of the most appealing...
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The scope, reactivity, and selectivity of the chiral hydroxamic acid-catalyzed kinetic resolution of chiral amines are improved by a new catalyst structure and a more environmentally friendly reaction protocol. In addition to increasing selectivity across all substrates, these conditions make possible the resolution of N-heterocycles containing lactams or other basic functional groups that can ...
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This paper considers the possibility of spontaneous transition of aracemic mixture (composed of equal amounts of two enantiomeric species, say L and D) into a monochiral state (in which only one enantiomer, say L, is present). Transitions of this kind have been recently experimentally observed. A plausible approach to this phenomenon is a model put forward by Frank, based on simple laws of ...
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Interest in saturated N-heterocycles as scaffolds for the synthesis of bioactive molecules is increasing. Reliable and predictable synthetic methods for the preparation of these compounds, especially medium-sized rings, are limited. We describe the development of SnAP (Sn amino protocol) reagents for the transformation of aldehydes into seven-, eight- and nine-membered saturated N-heterocycles....
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A rare example of the application of a catalytic, enantioselective Diels-Alder cycloaddition to affect a kinetic resolution has been developed. Chiral pyrazolidinones are resolved with high selectivity through a process that utilizes a relay of stereochemical information from a permanent chiral center to a fluxional chiral center to enhance the inherent selectivity of the chiral Lewis acid cata...
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ژورنال
عنوان ژورنال: Chemistry - A European Journal
سال: 2014
ISSN: 0947-6539
DOI: 10.1002/chem.201402818