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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."
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.
This term has become very popular and commonly used in practice. But the appropriate expression is "enantioselective chromatography". [34] Chiral chromatography has advanced to turn into the most preferred technique for the determination of enantiomeric purity as well as separation of pure enantiomers both on analytical and preparative scale.
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.
Chiral auxiliaries are incorporated into synthetic routes to control the absolute configuration of stereogenic centers. David A. Evans' synthesis of the macrolide cytovaricin, considered a classic, utilizes oxazolidinone chiral auxiliaries for one asymmetric alkylation reaction and four asymmetric aldol reactions, setting the absolute stereochemistry of nine stereocenters.
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The first example of an enantioselective nitroaldol reaction was reported in 1992 using Shibasaki catalysts. [11] One of the most frequently employed methods for inducing enantio- or diastereoselectivity in the Henry reaction is the use of chiral metal catalysts, in which the nitro group and carbonyl oxygen coordinate to a metal that is bound ...
In organic chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. [1] [2] It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added.