Highly enantioselective synthesis of cyclic sulfamidates and sulfamides via rhodium-catalyzed transfer hydrogenation.
نویسندگان
چکیده
We achieved highly enantioselective synthesis of cyclic 1,2-sulfamidates and -sulfamides via rhodium-catalyzed transfer hydrogenation, and also revealed one-pot preparation of cyclic N-sulfonylimines from α-hydroxy ketones.
منابع مشابه
Dynamic kinetic resolution in the stereoselective synthesis of 4,5-diaryl cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation.
The dynamic kinetic resolution of 4,5-diaryl cyclic sulfamidate imines was achieved via asymmetric transfer hydrogenation using a HCO(2)H/Et(3)N mixture as the hydrogen source and chiral Rh catalysts (R,R)- or (S,S)-RhCl(TsDPEN)Cp* affording the corresponding cyclic sulfamidates in good yields with up to >20 : 1 dr and up to >99% ee.
متن کاملAsymmetric synthesis of gem-diaryl substituted cyclic sulfamidates and sulfamides by rhodium-catalyzed arylation of cyclic ketimines.
Asymmetric addition of arylboronates to aryl-substituted cyclic ketimines proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of sulfamidates and sulfamides with high enantioselectivity (up to 99% ee).
متن کاملEnantioselective synthesis of cyclic sulfamidates via Pd-catalyzed hydrogenation.
Using Pd(CF3CO2) 2/(S,S)-f-binaphane as the catalyst, an efficient enantioselective synthesis of cyclic sulfamidates was developed via asymmetric hydrogenation of the corresponding cyclic imines in 2,2,2-trifluoroethanol at room temperature with high enantioselectivities (up to 99% ee).
متن کاملA Highly Enantioselective Brønsted Acid Catalyzed Cascade Reaction: Organocatalytic Transfer Hydrogenation of Quinolines and their Application in the Synthesis of AlkaloidsThe authors acknowledge Degussa AG for generous funding
The enantioselective hydrogenation of olefins, ketones, and imines still represents an important topic in organic synthesis and catalysis. Although many highly enantioselective processes based on chiral Rh, Ru, and Ir complexes have been reported, most of these catalysts failed to give satisfactory results in the asymmetric hydrogenation of aromatic and heteroaromatic compounds. Examples of eff...
متن کاملHighly enantioselective synthesis of sultams via Pd-catalyzed hydrogenation.
Using pd(cf(3)co(2))2/(S,S)-f-Binaphane as the catalyst, an efficient enantioselective synthesis of sultams was developed via asymmetric hydrogenation of the corresponding cyclic imines with high enantioselectivities. The hydrogenation products can be conveniently transformed to chiral homoallylic amines without loss of enantioselectivity.
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عنوان ژورنال:
- Chemical communications
دوره 47 8 شماره
صفحات -
تاریخ انتشار 2011