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Enantioselective synthesis, also called asymmetric synthesis, [1] is a form of chemical synthesis.It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts."
Definition and use A.C., [1] administrative case [2] N/A: English A case brought under administrative law in the form of a quasi-judicial proceeding by an agency of a non-judicial branch of government, or, the Office of the Court Administrator. Normally, such cases are internal disciplinary matters—court cases criminal and civil can be ...
An enantioselective reaction is one in which one enantiomer is formed in preference to the other, in a reaction that creates an optically active product from an achiral starting material, using either a chiral catalyst, an enzyme or a chiral reagent. The degree of selectivity is measured by the enantiomeric excess.
Desymmetrization is a chemical reaction that converts prochiral substrates into chiral products. Desymmetrisations are so pervasive that they are rarely described as such except when they proceed enantioselectively. The enantioselective reactions require chiral catalysts or chiral reagents. [1]
In this reaction, naturally occurring chiral proline is the chiral catalyst in an aldol reaction. The starting material is an achiral triketone and it requires just 3% of proline to obtain the reaction product, a ketol in 93% enantiomeric excess. This is the first example of an amino acid-catalyzed asymmetric aldol reaction. [16] [17]
In 1994, Kagan and co-workers reported a NLE in asymmetric sulfide oxidation. The goodness of fit for the reaction data matched the ML 4 model. This implied that a dimeric Titanium complexed with 4 DET ligands was the active catalytic species. [3] In this case, the reaction rate would be significantly faster relative to ideal reaction kinetics.
The Cram's rule of asymmetric induction named after Donald J. Cram states In certain non-catalytic reactions that diastereomer will predominate, which could be formed by the approach of the entering group from the least hindered side when the rotational conformation of the C-C bond is such that the double bond is flanked by the two least bulky groups attached to the adjacent asymmetric center. [3]
The Sharpless epoxidation is viable with a large range of primary and secondary alkenic alcohols. Furthermore, with the exception noted above, a given dialkyl tartrate will preferentially add to the same face independent of the substitution on the alkene.To demonstrate the synthetic utility of the Sharpless epoxidation, the Sharpless group created synthetic intermediates of various natural ...