The general procedure is described for the synthesis of product 6e via the copper-catalysed alkylation of ketimine 1e with n-HexMgBr. A Schlenk tube equipped with septum and stirring bar was charged with ketimine 1e 0. Dry MTBE 2. In a separate Schlenk tube, the corresponding Grignard reagent 0. The reaction was quenched with a saturated aqueous NH4Cl solution and the mixture was warmed to room temperature, diluted with dichloromethane and the phases were separated. The aqueous layer was extracted with dichloromethane 3 x 10 ml and the combined organic layers were dried with anhydrous MgSO4, filtered and the solvent was evaporated in vacuo.
Purification was performed by flash chromatography on silica gel using different mixtures of n-pentane:Et2O as the eluent and the enantiomeric excess was determined by chiral high-performance liquid chromatography analysis.
Data availability. The authors declare that the data supporting the findings of this study are available within the article and its Supplementary Information files. For the experimental procedures and spectroscopic and physical data of compounds, see Supplementary Methods. For NMR and high-performance liquid chromatography analysis of the compounds in this article, see Supplementary Figs Kobayashi, S.
Catalytic enantioselective formation of C-C bonds by addition to imines and hydrazones: a ten-year update. Yamada, K. Copper-catalyzed asymmetric alkylation of imines with dialkylzinc and related reactions. Shibasaki, M. Asymmetric synthesis of tertiary alcohols and a-tertiary amines via Cu-catalyzed C-C bond formation to ketones and ketimines. Yang, G. A palladium-catalyzed enantioselective addition of arylboronic acids to cyclic ketimines.
Nishimura, T. Asymmetric synthesis of triaryl methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines. Luo, Y. Enantioselective rhodium-catalyzed addition of potassium alkenyltrifluoroborates to cyclic imines. Lauzon, C. Catalytic asymmetric synthesis of a,a,a-trifluoromethylamines by the copper-catalyzed nucleophilic addition of diorganozinc reagents to imines.
Fu, P. Catalytic asymmetric alkylations of ketoimines. Hirner, S. Rhodium-catalyzed enantioselective addition of organoaluminum reagents to N-tosyl ketimines. Harutyunyan, S.
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Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents. Alexakis, A.
Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions. Jumde, R. P, Lanza, F. Catalytic asymmetric addition of Grignard reagents to alkenyl-substituted aromatic N-heterocycles. Science 22, Catalytic enantioselective addition of alkyl Grignard reagents to aliphatic aldehydes. Rong, J. Catalytic asymmetric alkylation of acylsilanes.
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CNB - Method for preparing chiral diaryl- substitute methylamine - Google Patents
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Manufacture of chiral amines using catalytic and flow processing methods
Han, X. Racemization of the newly created carbon-nitrogen stereo center is prevented because anions are stabilized at nitrogen i. The sulfinyl chiral auxiliary is readily removed by simple acid hydrolysis. The addition of organometallic reagents to N -sulfinyl imines is the most reliable and versatile method for the asymmetric synthesis of amine derivatives.
These building blocks have been employed in the asymmetric synthesis of numerous biologically active compounds. The first N -sulfinyl imines in racemic form were reported by Franklin A. Davis in by oxidation of p -toluene-sulfenyl imines with m-CPBA. Cinquini et al. The most widely used method for the asymmetric synthesis of N -sulfinyl imines is the condensation of enantiopure primary sulfinamides with aldehyde or ketones.
The two most commonly used are the Davis p -toluene-sulfinamide and the Ellman tert -butanesulfinamide   .
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An advantage of tert-butytsulfinyl imines is that acid treatment of the corresponding sulfinamides leads to easily removal by-products. From Wikipedia, the free encyclopedia. Chemical Society Reviews. Aldrichimica Acta. Home Subjects Chemistry Organic Chemistry. Selected type: Hardcover. Added to Your Shopping Cart. View on Wiley Online Library. This is a dummy description.