Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide

• Noble Brako,
• Sreerag Moorkkannur Narayanan,
• Amber Burns,
• Layla Auter,
• Valentino Cesiliano,
• Rajeev Prabhakar and
• Norito Takenaka

Beilstein J. Org. Chem. 2024, 20, 3069–3076, doi:10.3762/bjoc.20.255

• % yield with 61:39–92:8 enantiomeric ratios. Furthermore, possible mechanisms of propargyl–allenyl isomerization of propargyltrichlorosilane were computationally investigated. Keywords: α-allenic alcohol; computational chemistry; Lewis base catalysis; organocatalysis; propargyltrichlorosilane

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

• Matthias R. Steiner,
• Max Schmallegger,
• Larissa Donner,
• Johann A. Hlina,
• Christoph Marschner,
• Judith Baumgartner and
• Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

• reactive in chloroform solution, while in methanol the corresponding phosphonium phenolate is formed. Keywords: Lewis-base catalysis; Michael acceptor reactivity; phospha-Michael reaction; phosphonium phenolate zwitterion; Introduction Organocatalysis has emerged in recent years as a valuable and

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• Brønsted acid-assisted Lewis base catalysis. Synthesis of CF3-pyrazoles and CF3-1,6-dihydropyridazines. Asymmetric reactions of trifluoromethylimines with organometallic reagents. Mannich-type reaction of trifluoroacetaldehyde hydrazones. Synthesis of trifluoromethylated hydrazonoyl halides. Early work of

• pairs and provides a good basis and scope for further extensions and explorations [39] (Scheme 3). Based on the work by Wu et al. and extending their previous work, Rueping and co-workers explored the effects of fluorine in organocatalytic reactions. They developed an asymmetric Brønsted acid–Lewis base

• catalysis, for the synthesis of trifluoromethylated dihydropyridazines under simple reaction conditions and the chemistry displayed very good enantioselectivities and high functional group tolerance (Scheme 4) [40]. Zhan et al. reported an efficient and highly selective method for the synthesis of CF3

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• azepane. A possible mechanism was suggested for this Lewis base catalysis system. Methanesulfonic acid (MsOH) activated reagent 14, which coordinated with the Lewis base (S)-E, to form complex I. Then, the transfer of the sulfenium ion to the alkene resulted in chiral thiiranium ion II. Capture of the

The chemistry of amine radical cations produced by visible light photoredox catalysis

• Jie Hu,
• Jiang Wang,
• Theresa H. Nguyen and
• Nan Zheng

Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234

• . In 2011, Rueping and coworkers described a dual catalytic system combining photoredox and Lewis base catalysis for the functionalization of C–H bonds α to the nitrogen atom of N-aryltetrahydroisoquinoline 13 (Scheme 8) [65]. In the presence of a Lewis base, a ketone is converted to enamine

• . Oxidative functionalization of N-aryltetrahydroisoquinolines using Eosin Y. Synthetic and mechanistic studies of Eosin Y-catalyzed aza-Henry reaction. Oxidative functionalization of N-aryltetrahydroisoquinolines using RB and GO. Merging Ru-based photoredox catalysis and Lewis base catalysis for the Mannich

• reaction. Merging Au-based photoredox catalysis and Lewis base catalysis for the Mannich reaction. Merging Ru-based photoredox catalysis and Cu-catalyzed alkynylation reaction. Merging Ru-based photoredox catalysis and NHC catalysis. 1,3-Dipolar cycloaddition of photogenically formed azomethine ylides

Cation affinity numbers of Lewis bases

• Christoph Lindner,
• Raman Tandon,
• Boris Maryasin,
• Evgeny Larionov and
• Hendrik Zipse

Beilstein J. Org. Chem. 2012, 8, 1406–1442, doi:10.3762/bjoc.8.163

• that the (R)- and the (S)-enantiomer do not have to have the same affinity values. For the phosphane 317 the difference is below 2 kJ/mol, but for phosphane 316 the difference is 21 kJ/mol. A last group of nucleophiles employed in Lewis-base catalysis concerns nucleophilic carbenes (Table 8) [14][15

Kinetics and mechanism of vanadium catalysed asymmetric cyanohydrin synthesis in propylene carbonate

• Michael North and
• Marta Omedes-Pujol

Beilstein J. Org. Chem. 2010, 6, 1043–1055, doi:10.3762/bjoc.6.119

• that Lewis base catalysis made a much greater contribution to the overall catalytic activity of VO(salen)NCS in propylene carbonate than in dichloromethane. Keywords: cyanohydrin; Hammett; kinetics; propylene carbonate; vanadium; Introduction The last 15 years have witnessed an explosion of activity

• Lewis base catalysis are known to be involved in the catalytic cycle, the latter possibly involving the isothiocyanate counterion [52]. Despite their many favourable properties, there is one drawback associated with catalysts 1 and 2; they exhibit highest activity and highest enantioselectivity in

• , which allow differences in the relative importance of Lewis acid and Lewis base catalysis between reactions carried out in dichloromethane and propylene carbonate to be elucidated. Results and Discussion Synthetic Studies Initially, the compatibility of catalysts 1 and 2 with propylene carbonate was