Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• oxygen ene reaction involving the electron-rich olefin allowed the formation of an aldehyde, which was directly cleaved by an iridium-catalyzed deformylation, affording 52 in one-pot [36]. Deprotonation with KHMDS allowed the formation of an electron-rich diene which could again react with singlet oxygen

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

• Girish Suresh Yedase,
• Sumit Kumar,
• Jessica Stahl,
• Burkhard König and
• Veera Reddy Yatham

Beilstein J. Org. Chem. 2021, 17, 1727–1732, doi:10.3762/bjoc.17.121

• generating oxygen-centered radicals, that lead to carbon-centered radicals through intra/intermolecular hydrogen atom transfer (HAT) processes, radical decarboxylative or radical deformylation [57][58][59]. In continuation of our research interest on visible-light-driven cerium photocatalysis [59][65], we

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

• Yuichi Yoshimura,
• Hideaki Wakamatsu,
• Yoshihiro Natori,
• Yukako Saito and
• Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

• , similar deformylation by action of hypervalent iodine has also been demonstrated: the β-fragmentation reaction of an anomeric alkoxy radical of carbohydrates was mediated by a hypervalent iodine reagent [73]. The reaction results in the formation of carbohydrates with a reduction of one carbon. From the

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• -catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the

• synthetic versatility of quinone-catalyzed oxidative C–C bond cleavage. Keywords: catalysis; deformylation; organic synthesis; organocatalysis; Introduction Imines are extremely versatile intermediates in organic chemistry [1][2][3]. Consequently, many synthetic methods have been developed for the

• common [29][30][31][32] despite the fact that these methods employ renewable resources, such as amino acids and their derivatives, as starting materials. In fact, only a few reports describing the oxidative deformylation of amino alcohols have been published [33][34][35], and in all of these reports

Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

• Larisa Yu. Gurskaya,
• Diana S. Belyanskaya,
• Dmitry S. Ryabukhin,
• Denis I. Nilov,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 950–956, doi:10.3762/bjoc.12.93

• two positive charges in C substantially increases the electrophilic properties of the carbon of the O-protonated N-formyl group and explains its reactivity. The reactions of 5 with other arenes, such as 1,2-dichlorobenzene, toluene, or isomeric xylenes, gave deformylation products 2. In this case