1059044-01-7Relevant academic research and scientific papers
METHOD FOR THE PRODUCTION OF OPTICALLY ACTIVE ALPHA ALKYL CARBONYL COMPOUNDS
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Page/Page column 6, (2010/12/29)
A method for the production of optically active α-alkylcarbonyl compounds with retention of the stereo information of the starting compound. The starting compound used here is a carbonyl compound which has, in the α-position, a leaving group which is substituted by an alkyl group with inversion of the configuration. The substitution of the leaving group is effected with the use of an alkylmagnesium Grignard and a zinc (II) salt or a zinc organyl. The method permits the production of optically active α-alkylcarbonyl compounds at very mild temperatures (for example 0° C.) with the use of starting compounds which are easy to prepare and economical and nontoxic catalysts, it also being possible to achieve a very high yield.
Zinc-catalyzed enantiospecific sp3-sp3 cross-coupling of α-hydroxy ester triflates with grignard reagents
Studte, Christopher,Breit, Bernhard
supporting information; experimental part, p. 5451 - 5455 (2009/03/12)
(Chemical Equation Presented) Zinc chloride does the trick and efficiently catalyzes the enantiospecific cross-coupling of α-hydroxy ester triflates with Grignard reagents under mild conditions. Enantiopure α-hydroxy esters are directly available from the chiral pool or by diazotization of α-amino acids. Substantial variations in both reacting partners are tolerated making this methodology an attractive alternative to enolate alkylation featuring a reversal of polarity.
