Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction

Shi-Ming Xu, Liang Wei, Chong Shen, Lu Xiao, Hai-Yan Tao and Chun-Jiang Wang ()
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Shi-Ming Xu: Wuhan University
Liang Wei: Wuhan University
Chong Shen: Wuhan University
Lu Xiao: Wuhan University
Hai-Yan Tao: Wuhan University
Chun-Jiang Wang: Wuhan University

Nature Communications, 2019, vol. 10, issue 1, 1-11

Abstract: Abstract Enantiomerically enriched indole-containing heterocycles play a vital role in bioscience, medicine, and chemistry. As one of the most attractive subtypes of indole alkaloids, highly substituted tetrahydro-γ-carbolines are the basic structural unit in many natural products and pharmaceuticals. However, the syntheses of tetrahydro-γ-carbolines with high functionalities from readily available reagents are significant challenging. In particular, the stereodivergent syntheses of tetrahydro-γ-carbolines containing multi-stereogenic centers remain quite difficult. Herein, we report an expedient and stereodivergent assembly of tetrahydro-γ-carbolines with remarkably high levels of stereoselective control in an efficient cascade process from aldimine esters and indolyl allylic carbonates via a synergistic Cu/Ir catalyst system. Control experiments-guided optimization of synergistic catalysts and mechanistic investigations reveal that a stereodivergent allylation reaction and a subsequent highly stereoselective iso-Pictet-Spengler cyclization are the key elements to success.

Date: 2019
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DOI: 10.1038/s41467-019-13529-z

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