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Asymmetric synthesis of an atropisomeric β-carboline via regioselective intermolecular Rh(I)-catalyzed [2 + 2 + 2] cyclotrimerization

https://doi.org/10.1016/j.tetlet.2024.155187

Hughes, Riley R; Battistoni, Lorenzo D; Ciesla, Matthew J; Bolton, Te’jandrio; Asher, Patrick M; Irizarry, Giancarlo; de_Jesus_Antonio_Martinez, Alma; Baker, Kristen M; Mulcahy, Seann P (August 2024, Tetrahedron Letters)

The rational design of atropisomeric small molecules is becoming increasingly common in chemical synthesis as a result of the unique advantages this property provides in drug discovery, asymmetric catalysis, and chiroptical activity. In this study, we designed a synthesis of a configurationally stable β-carboline in six steps. Our synthesis made use of an innovative Grignard addition/elimination reaction that formed an yne-ynamide precursor that then reacted with ethyl cyanoformate in a rhodium(I)-catalyzed [2 + 2 + 2] cyclotrimerization reaction to give the atropisomeric β-carboline in excellent yield, good enantioselectivity, and excellent regioselectivity. Extensive optimization of this transformation is described. Racemization kinetics experiments were also conducted on the individual atropisomers and their absolute configurations were determined by circular dichroism.
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Design, Synthesis, and Physicochemical Studies of Configurationally Stable β-Carboline Atropisomers

https://doi.org/10.1021/acs.joc.2c01675

Baker, Kristen M.; Agostino, Colby J.; Orloff, Emily A.; Battistoni, Lorenzo D.; Hughes, Riley R.; McHugh, Erin M.; Shaw, Michael P.; Nafie, Jordan; Mulcahy, Seann P. (September 2022, The Journal of Organic Chemistry)

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Metal-Catalyzed Cyclotrimerization Reactions of Cyanamides: Synthesis of 2-Aryl-α-carbolines

https://doi.org/10.1021/acs.orglett.0c00891

Medas, Kyle M.; Lesch, Robert W.; Edioma, Friendship B.; Wrenn, Sean P.; Ndahayo, Vincent; Mulcahy, Seann P. (April 2020, Organic Letters)

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Parallel strategies for the synthesis of annulated pyrido[3,4-b]indoles via Rh(I)- and Pd(0)-catalyzed cyclotrimerization

https://doi.org/10.1016/j.tetlet.2018.10.050

Saliba, Bianca M.; Khanal, Satyam; O'Donnell, Michael A.; Queenan, Kathryn E.; Song, Junho; Gentile, Matthew R.; Mulcahy, Seann P. (December 2018, Tetrahedron Letters)

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