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Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction
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Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction
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Journal Article
Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction
2019
Overview
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.
Tetrahydro-γ-carbolines are the basic structural unit in many natural products and pharmaceuticals. Here, the authors report a synergistic Cu/Ir system to assemble chiral tetrahydro-γ-carbolines via a stereodivergent allylation followed by a stereoselective iso-Pictet-Spengler cyclization.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
/ 140/58
/ Assembly
/ Carbolines - chemical synthesis
/ Carbon
/ Chromatography, High Pressure Liquid
/ Esters
/ Humanities and Social Sciences
/ Indole Alkaloids - chemical synthesis
/ Indole Alkaloids - chemistry
/ Indoles
/ Indoles - chemical synthesis
/ Proton Magnetic Resonance Spectroscopy
/ Reagents
/ Science
