Chemistry is traditionally divided into organic and inorganic chemistry. Formula: C10H11NO, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 27404-31-5
Diverse asymmetric quinolizidine synthesis: A stereodivergent one-pot approach
A diverse stereodivergent organocatalytic one-pot addition/cyclization/ annulation sequence to optically active quinolizidine derivatives from easily available starting materials is presented. The one-pot sequence relies on a pyrrolidine-catalyzed enantioselective conjugate addition of electron-deficient amide a-carbons to alpha,beta-unsaturated aldehydes, spontaneous hemiaminal formation and acid-catalyzed/mediated N-acyliminium ion cyclization to give the quinolizidine framework. Simple tuning of the reaction conditions in the N-acyliminuim ion cyclization step provides a diastereomeric switch, which gives access to both of the two bridgehead epimers through kinetic, thermodynamic or chelation control. The methodology display a broad substrate scope that is demonstrated by the stereoselective formation of indolo-, thieno-, benzofuro-, furo- and different benzoquinolizidine derivatives with high atom efficiency, up to >99% ee and up to >95:5 dr. Due to its efficiency, synthetic diversity and operational simplicity, this protocol has the potential to find important use as a key step in natural product synthesis, biochemistry and pharmaceutical science. The stereochemical outcome of the one-pot sequence was investigated, and the mechanism and origin of stereoselectivity of the different steps is discussed.
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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1609O – PubChem