Enantioselective cooperative triple catalysis: unique roles of Au(I)/amine/chiral Brønsted acid catalysts in the addition/cycloisomerization/transfer hydrogenation cascade.
نویسندگان
چکیده
An enantioselective cooperative process involving the concerted/simultaneous action of three different catalysts i.e. Au(I)/amine/chiral Brønsted acid catalysts has been realized for the synthesis of 2-substituted tetrahydroquinolines from 2-aminobenzaldehydes and terminal alkynes.
منابع مشابه
A 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...
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متن کاملTuning the reactivity of Au-complexes in an Au(I)/chiral Brønsted acid cooperative catalytic system: an approach to optically active fused 1,2-dihydroisoquinolines.
An enantioselective cooperative catalysis protocol, utilizing achiral Au(I) complexes and chiral Brønsted acids, has been developed for the synthesis of optically pure fused 1,2-dihydroisoquinolines starting from 2-alkynylbenzaldehydes and 2-aminobenzamides.
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Herein we report an enantioselective synthesis of complex cyclopentanones using aliphatic aldehydes and activated enones. With the combination of a chiral secondary amine and a chiral triazolium catalyst, high diastereoselectivity and excellent enantioselectivity can be achieved. We present evidence of a clear cooperative effect when these two catalysts are present simultaneously in the system.
متن کاملA combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines
A continuous-flow asymmetric organocatalytic photocyclization-transfer hydrogenation cascade reaction has been developed. The new protocol allows the synthesis of tetrahydroquinolines from readily available 2-aminochalcones using a combination of photochemistry and asymmetric Brønsted acid catalysis. The photocylization and subsequent reduction was performed with catalytic amount of chiral BINO...
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ورودعنوان ژورنال:
- Chemical communications
دوره 49 6 شماره
صفحات -
تاریخ انتشار 2013