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Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: enantioselective total synthesis of (-)-mesembrine. 2012

Qian-Qian Zhang, and Jian-Hua Xie, and Xiao-Hui Yang, and Jian-Bo Xie, and Qi-Lin Zhou
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.

A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).

UI MeSH Term Description Entries
D007495 Iridium A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.
D007659 Ketones Organic compounds containing a carbonyl group Ketone
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D006865 Hydrogenation Addition of hydrogen to a compound, especially to an unsaturated fat or fatty acid. (From Stedman, 26th ed) Hydrogenations
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D020005 Propanols Isomeric forms and derivatives of PROPANOL (C3H7OH). Alcohols, Propyl,Propyl Alcohols
D020650 Combinatorial Chemistry Techniques A technology, in which sets of reactions for solution or solid-phase synthesis, is used to create molecular libraries for analysis of compounds on a large scale. Chemistry Techniques, Combinatorial,Techniques, Combinatorial Chemistry,Chemistry Technic, Combinatorial,Chemistry Technics, Combinatorial,Chemistry Technique, Combinatorial,Combinatorial Chemistry Technic,Combinatorial Chemistry Technics,Combinatorial Chemistry Technique,Technic, Combinatorial Chemistry,Technics, Combinatorial Chemistry,Technique, Combinatorial Chemistry
D026121 Indole Alkaloids Group of alkaloids containing a benzylpyrrole group (derived from TRYPTOPHAN). Indole Alkaloid,Alkaloid, Indole,Alkaloids, Indole

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