1174005-78-7Relevant academic research and scientific papers
Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of Hetero-triarylmethanes from Racemic Indolyl Alcohols
Yue, Caizhen,Na, Fei,Fang, Xiantao,Cao, Yang,Antilla, Jon C.
, p. 11004 - 11008 (2018)
The direct enantioselective 1,4- and 1,8-arylations of 7-methide-7H-indoles and 6-methide-6H-indoles, respectively, generated in situ from diarylmethanols, with electron-rich arenes as nucleophiles, has been achieved in the presence of chiral phosphoric acids (CPAs). These two remote activation protocols provide an efficient approach for the construction of diverse hetero-triarylmethanes in high yields (up to 97 %) and with excellent enantioselectivities (up to 96 %). Mechanistically inspired experiments tentatively indicate that the catalytic enantioselective 1,4-addition as well as the formal SN1 substitution could proceed efficiently in the similar catalytic systems. Furthermore, the modification of the catalytic system and diarylmethanol structure successfully deviates the reactivity toward a remote, highly enantioselective 1,8-arylation reaction. This flexible activation mode and novel reactivity of diarylmethanols expand the synthetic potential of chiral phosphoric acids.
Aminocatalyzed Cascade Synthesis of Enantioenriched 1,7-Annulated Indoles from Indole-7-Carbaldehyde Derivatives and α,β-Unsaturated Aldehydes
Giardinetti, Maxime,Moreau, Xavier,Coeffard, Vincent,Greck, Christine
, p. 3501 - 3506 (2016/01/25)
We report herein a new cascade strategy for the enantioselective synthesis of 1,7-annulated indoles based on iminium-enamine activation. A careful study of the indole substitution pattern revealed that a chloro substituent at the C-3 position was importan
