L-Valine derived chiral N-sulfinamides as effective organocatalysts for the asymmetric hydrosilylation of N-alkyl and N-aryl protected ketimines.
نویسندگان
چکیده
L-Valine derived N-sulfinamides have been developed as efficient enantioselective Lewis basic organocatalysts for the asymmetric reduction of N-aryl and N-alkyl ketimines with trichlorosilane. Catalyst 3c afforded up to 99% yield and 96% ee in the reduction of N-alkyl ketimines and up to 98% yield and 98% ee in the reduction of N-aryl ketimines.
منابع مشابه
Convenient, enantioselective hydrosilylation of imines in protic media catalyzed by a Zn-trianglamine complex.
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ABSTRACT Chiral acyclic and macrocyclic amines derived from trans-1,2-diaminocyclohexane in complexes with diethylzinc efficiently catalyze asymmetric hydrosilylation of aryl-alkyl and aryl-aryl ketones with enantiomeric excess of the product up to 86 %. A trianglamine ligand with a cyclic structure or the presence of an additional coordinating group increases the enantioselectivity of the reac...
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Twelve P-chiral phosphine oxides were screened for their ability to act as a chiral Lewis base catalyst for the asymmetric hydrosilylation of ketimines, providing chiral amines in good conversion and yield, but relatively poor enantioselectivity (ee <30%). Mechanistic studies paralleling work on chiral sulfinamides have shown a non-linear relationship of catalyst enantioselectivity and the chir...
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L-Pipecolinic acid derived Lewis basic N-formamide has been developed as a first highly effective catalyst for the asymmetric reduction of aromatic and aliphatic ketones as well as aromatic and aliphatic ketimines in good to high enantioselectivity.
متن کاملThe use of chiral lithium amides in the desymmetrisation of N-trialkylsilyl dimethyl sulfoximines
BACKGROUND Chiral base desymmetrisation of dimethyl sulfoximines could provide a general route to chiral, enantioenriched dialkyl sulfoximines with potential for use in asymmetric catalysis. RESULTS Asymmetric deprotonation of N-trialkylsilyl dimethyl sulfoximines with either enantiomer of lithium N,N-bis(1-phenylethyl)amide in the presence of lithium chloride affords enantioenriched sulfoxim...
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 2 شماره
صفحات -
تاریخ انتشار 2015