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For the α,β unsaturated systems 10-12, efficient reduction of the ketone occurs despite the possible side reaction of hydroboration of the C-C unsaturated bond. The CBS reduction has also been shown to tolerate the presence of heteroatoms as in ketone 13, which is capable of coordinating to the borane.
Enantioselective ketone reductions convert prochiral ketones into chiral, non-racemic alcohols and are used heavily for the synthesis of stereodefined alcohols. [ 1 ] Carbonyl reduction, the net addition of H 2 across a carbon-oxygen double bond, is an important way to prepare alcohols.
The aluminium based Meerwein–Ponndorf–Verley reduction can be performed on prochiral ketones leading to chiral alcohols. The three main ways to achieve the asymmetric reduction is by use of a chiral alcohol hydride source, use of an intramolecular MPV reduction, or use of a chiral ligand on the aluminium alkoxide.
In stereochemistry, prochiral molecules are those that can be converted from achiral to chiral in a single step. [1] [2] An achiral species which can be converted to a chiral in two steps is called proprochiral. [2] If two identical substituents are attached to an sp 3-hybridized atom, the descriptors pro-R and pro-S are used to distinguish ...
Corey–Bakshi–Shibata reduction (CBS reduction)-1. In 1987, Elias James Corey and co-workers found out that the formation of oxazaborolidines from borane and chiral amino alcohols. And the oxazaborolidines were found to catalyze the rapid and highly enantioselective reduction of prochiral ketones in the presence of BH3THF.
Barbas' collaborator List also extended the reaction to asymmetric prochiral ketones: List and Notz also revealed that proline and 5,5-dimethyl thiazolidinium-4-carboxylate appeared to be optimal catalysts within a large group of screened amines. [14] In 2002 the Macmillan group demonstrated a proline-catalyzed aldol reaction between aldehydes ...
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An enantioselective (80 to 92% ee) reduction of prochiral α,β-unsaturated esters uses Tol-BINAP complexes of copper in the presence of PMHS as the reductant. [24] Subsequently, conditions have been developed for the CuH-catalyzed hydrosilylation of ketones [25] and imines [26] proceeding with excellent levels of chemo- and enantioselectivity.