Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds

• Gerold Heuger and
• Richard Göttlich

Beilstein J. Org. Chem. 2015, 11, 1226–1234, doi:10.3762/bjoc.11.136

• aminohalogenation of cinnamic esters using N,N-dichloro-p-toluenesulfonamide and ZnCl2 or Cu(OTf)2 [18] as catalysts and transferred these conditions to reactions with alkynes [19][20][21] and α,β-unsaturated ketones [19][20][21]. An ionic mechanism via halonium ions was proposed. The amidofluorination of alkenes

One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular S_N2 reaction

• Yiwen Xiong,
• Ping Qian,
• Chenhui Cao,
• Haibo Mei,
• Jianlin Han,
• Guigen Li and
• Yi Pan

Beilstein J. Org. Chem. 2014, 10, 1802–1807, doi:10.3762/bjoc.10.189

• directly from cinnamate esters using N,N-dichloro-p-toluenesulfonamide and benzylamine as nitrogen sources. The key transformations include a Cu-catalyzed aminohalogenation and aziridination, followed by an intermolecular SN2 nucleophilic ring opening by benzylamine. The reactions feature a wide scope of

• substrates and proceed with excellent stereo- and regioselectivity (anti:syn >99:1) . Keywords: aminohalogenation; diamination; α,β-diamino ester; one-pot; stereoselectivity; Introduction α,β-Diamino acid derivatives are one of the most important classes of nitrogen-containing bioactive compounds [1][2

• . However, these methods suffer from the shortcomings, such as need of special starting materials, use of expensive metal catalysts or strict anhydrous and anaerobic conditions. The aminohalogenation reaction has been well studied in the past decade [29][30][31][32], and the corresponding vicinal haloamine

Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy

• Daisuke Shigeoka,
• Takuma Kamon and
• Takehiko Yoshimitsu

Beilstein J. Org. Chem. 2013, 9, 860–865, doi:10.3762/bjoc.9.99

• Daisuke Shigeoka Takuma Kamon Takehiko Yoshimitsu Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan 10.3762/bjoc.9.99 Abstract An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key

• intermediate for the synthesis of (−)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N–iron intermediates in the

• redox states were operative. Keywords: agelastatin; aminohalogenation; iron(II); free radical; natural product synthesis; Introduction Marine organisms often produce bioactive substances that potentially serve as attractive resources for drug discovery. (−)-Agelastatin A (AA, 1), a cytotoxic alkaloid

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• acetonitrile as the solvent, allowed the formation of the dihalogenated pyrazino[1,2-a]indole derivatives 52 by an unusual aminohalogenation/halogenation sequence (Scheme 30). The formation of the 3-haloderivatives XXI, ascribable solely to the action of the Cu(II) salt [84], and the cyclization of the π