In an article, author is Zhou, Zijun, once mentioned the application of 3082-64-2, Name is (R)-1-Phenylpropan-1-amine, molecular formula is C9H13N, molecular weight is 135.2062, MDL number is MFCD00083057, category is chiral-catalyst. Now introduce a scientific discovery about this category, Category: chiral-catalyst.
Chiral beta-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric beta-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp(3))-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral beta-amino alcohols. Specifically, the ring-closing C(sp(3))-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp(3))-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral beta-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral beta-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.
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Reference:
Chiral Catalysts,
,Chiral catalysts – SlideShare