» Articles » PMID: 38639395

Photocatalytic Enantioselective Radical Cascade Multicomponent Minisci Reaction of β-Carbolines Using Diazo Compounds As Radical Precursors

Overview
Journal Adv Sci (Weinh)
Date 2024 Apr 19
PMID 38639395
Authors
Affiliations
Soon will be listed here.
Abstract

Here, a photocatalytic asymmetric multicomponent cascade Minisci reaction of β-carbolines with enamides and diazo compounds is reported, enabling an effective enantioselective radical C─H functionalization of β-carbolines with high yields and enantioselectivity (up to 83% yield and 95% ee). This enantioselective multicomponent Minisci protocol exhibits step economy, high chemo-/enantio-selective control, and good functional group tolerance, allowing access to a variety of valuable chiral β-carbolines. Notably, diazo compounds are suitable radical precursors in enantioselective cascade radical reactions. Moreover, the efficiency and practicality of this approach are demonstrated by the asymmetric synthesis of bioactive compounds and natural products.

Citing Articles

Photocatalytic Enantioselective Radical Cascade Multicomponent Minisci Reaction of β-Carbolines Using Diazo Compounds as Radical Precursors.

Gu Y, Luo M, Yuan H, Liu G, Wang S Adv Sci (Weinh). 2024; 11(25):e2402272.

PMID: 38639395 PMC: 11220658. DOI: 10.1002/advs.202402272.

References
1.
Domling A, Wang W, Wang K . Chemistry and biology of multicomponent reactions. Chem Rev. 2012; 112(6):3083-135. PMC: 3712876. DOI: 10.1021/cr100233r. View

2.
Rashid M, Gustafson K, Boyd M . New cytotoxic N-methylated beta-carboline alkaloids from the marine ascidian Eudistoma gilboverde. J Nat Prod. 2001; 64(11):1454-6. DOI: 10.1021/np010214+. View

3.
Humphrey J, Liao Y, Ali A, Rein T, Wong Y, Chen H . Enantioselective total syntheses of manzamine a and related alkaloids. J Am Chem Soc. 2002; 124(29):8584-92. DOI: 10.1021/ja0202964. View

4.
Ingallina C, DAcquarica I, Delle Monache G, Ghirga F, Quaglio D, Ghirga P . The Pictet-Spengler Reaction Still on Stage. Curr Pharm Des. 2016; 22(12):1808-50. DOI: 10.2174/1381612822666151231100247. View

5.
Colgan A, Proctor R, Gibson D, Chuentragool P, Lahdenpera A, Ermanis K . Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols. Angew Chem Int Ed Engl. 2022; 61(25):e202200266. PMC: 9321721. DOI: 10.1002/anie.202200266. View