Wang, Yidong; Zhang, Peichao; Di, Xiaoyu; Dai, Qiang; Zhang, Zhan-Ming; Zhang, Junliang published the article 《Gold-Catalyzed Asymmetric Intramolecular Cyclization of N-Allenamides for the Synthesis of Chiral Tetrahydrocarbolines》. Keywords: gold catalyzed asym intramol cyclization allenamide chiral hydrocarboline synthesis; chiral sulfinamide phosphine ligand gold catalyzed asym intramol cyclization; desbromoarborescidine A synthesis desbromoarborescidine C formal synthesis; deplancheine formal synthesis; desymmetrization allenamide; allenamides; cyclization; enantioselectivity; gold; tetrahydrocarboline.They researched the compound: (R)-N-((R)-(5-(Diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl)(4-methoxyphenyl)methyl)-2-methylpropane-2-sulfinamide( cas:2160535-56-6 ).Application In Synthesis of (R)-N-((R)-(5-(Diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl)(4-methoxyphenyl)methyl)-2-methylpropane-2-sulfinamide. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:2160535-56-6) here.
Highly enantioselective gold-catalyzed intramol. cyclization of N-allenamides was implemented by utilizing a designed chiral sulfinamide phosphine ligand (PC-Phos) [e.g., allenamide I → tetrahydrocarboline II (99%, 96% ee) in presence of Me2S.AuCl, AgNTf2 and ligand III in CH2Cl2 at -50°]. This represents the first example of highly enantioselective intramol. cyclization of N-allenamides. The practicality of this reaction was validated in the total synthesis of (R)-desbromoarborescidine A and formal synthesis of (R)-desbromoarborescidine C and (R)-deplancheine. Moreover, the catalyst system PC-Phos/AuNTf2 proved to be specifically efficient to promote the desymmetrization of N-allenamides in excellent yields with satisfactory ee values.
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