Catalytic multi-step domino and one-pot reactions

• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

• mixed in one flask, in which all reaction steps take place autonomously without the addition of further reactants [1]. The domino process contrasts the conventional "stop-and-go" synthetic approach in the way that multiple reactions proceed in a direct sequence. In such a reaction sequence, one step

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal

• Alessandro Brusa,
• Debora Iapadre,
• Maria Edith Casacchia,
• Alessio Carioscia,
• Giuliana Giorgianni,
• Giandomenico Magagnano,
• Fabio Pesciaioli and
• Armando Carlone

Beilstein J. Org. Chem. 2023, 19, 1243–1250, doi:10.3762/bjoc.19.92

• . Although the scope is limited to aromatic nitroalkenes and enals, the yields are good considering the complexity of the domino process that involves highly reactive partners, and the ees are consistently very high. Finally, albeit there is low diastereocontrol, the diastereomers can be easily separated by

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• % ee) (Table 1, entry 1). Due to the excellent stereoselectivity of the target product 3aa, the reaction conditions were further optimized to increase its yield. Subsequently, a number of organocatalysts (Figure 3) were evaluated for this domino process (Table 1, entries 2–8). From the experimental

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

• Natascha Breuer,
• Irina Gruber,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

• effects of base and temperature on Michael addition–cyclocondensation sequences in the formation of α-pyrones and/or 1H-pyridines starting from diversely substituted alkynones and cyanoethylacetate. This bifurcating domino process furnishes small chromophore libraries which were characterized by

Domino ring-opening–ring-closing enyne metathesis vs enyne metathesis of norbornene derivatives with alkynyl side chains. Construction of condensed polycarbocycles

• Ritabrata Datta and
• Subrata Ghosh

Beilstein J. Org. Chem. 2018, 14, 2708–2714, doi:10.3762/bjoc.14.248

• functional group and the substrate structure and may follow a different reaction course than what is usually observed. In cases where ROM–RCEYM occurred, the resulting 1,3-diene reacts in situ with the dienophile to provide condensed tetracyclic systems. Keywords: Diels–Alder reaction; domino process; enyne

• metathesis; natural products; polycarbocycles; Introduction The metathesis of norbornene derivatives having an alkene side-chain on the norbornene nucleus with Grubbs’ ruthenium catalysts has been extensively investigated. Generally the reaction proceeds through a domino process involving a ring opening of

• ][28][29][30][31][32][33] for the synthesis of a variety of complex ring systems such as condensed, bridged and spirocycles difficult to obtain otherwise. On the contrary, the domino process involving a ring-opening metathesis (ROM) followed by a ring-closing enyne metathesis (RCEYM) [34][35][36][37

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

• Gwendal Grelier,
• Benjamin Darses and
• Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

• domino process for the introduction of both aromatic rings of diaryl-λ3-iodanes, though a small excess of this reagent is needed to obtain good yields. An initial N-arylation reaction of 3,5-dimethylpyrazole is performed in the presence of potassium carbonate, in xylene at 70 °C, releasing 1 equivalent

Unusual reactions of diazocarbonyl compounds with α,β-unsaturated δ-amino esters: Rh(II)-catalyzed Wolff rearrangement and oxidative cleavage of N–H-insertion products

• Valerij A. Nikolaev,
• Jury J. Medvedev,
• Olesia S. Galkina,
• Ksenia V. Azarova and
• Christoph Schneider

Beilstein J. Org. Chem. 2016, 12, 1904–1910, doi:10.3762/bjoc.12.180

• provides a good way for the synthesis of multi-functionalized N-arylpyrrolidines by the same “metal–carbene” methodology with yields of up to 82% [15]. The reactions occur as a domino process involving an initial formation of N-ylides A followed by the intramolecular Michael addition with the conjugated

Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides

• Lena Huck,
• Juan F. González,
• Elena de la Cuesta and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2016, 12, 1772–1777, doi:10.3762/bjoc.12.166

• double bond in readily available 3-arylmethylene-2,5-piperazinediones, followed by a domino process involving three consecutive nucleophilic attacks that achieve regioselective opening of the diketopiperazine ring and diastereoselective generation of the aziridine ring. The protocol described here

Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp³)–H arylation

• Yunyun Liu,
• Yi Zhang,
• Xiaoji Cao and
• Jie-Ping Wan

Beilstein J. Org. Chem. 2016, 12, 1122–1126, doi:10.3762/bjoc.12.108

• known syntheses, a domino process by which the AQ can be linked directly to the raw substrates to enable the subsequent arylation transformation in one pot would be highly favorable for enhancing step economy. Upon this assumption as well as our interest in both domino reactions and C–H

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

• Giorgos Koutoulogenis,
• Nikolaos Kaplaneris and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2016, 12, 462–495, doi:10.3762/bjoc.12.48

• stereochemistry of the carbon bearing the R2 group. Very recently, Wang and co-workers used a cinchona alkaloid-based bifunctional thiourea 103 as the catalyst of choice to an organocatalytic domino process. This domino reaction involded a Michael cyclization–tautomerization reaction sequence between isatylidene

• enantioselective synthesis of 3,4-dihydrocoumarins 150 bearing an all-carbon spiro-quaternary stereocenter utilizing Takemoto’s organocatalyst 77 (Scheme 48) [69]. The domino process is initiated by a Michael addition followed by acetalization, and subsequent PCC oxidation in an one-pot transformation. In 2012

• , Liang, Xu and co-workers developed a domino process in order to construct polysubstituted chromeno[4,3-b]pyrrolidine derivatives 157, utilizing a bifunctional organocatalyst 57 (Scheme 50) [71]. The transformation is quite powerful, utilizing under mild conditions and a very low catalyst loading. The

Visible-light-induced, Ir-catalyzed reactions of N-methyl-N-((trimethylsilyl)methyl)aniline with cyclic α,β-unsaturated carbonyl compounds

• Dominik Lenhart and
• Thorsten Bach

Beilstein J. Org. Chem. 2014, 10, 890–896, doi:10.3762/bjoc.10.86

• higher type selectivity. The domino process was suppressed and the plain addition product 22 was obtained in 75% yield (Scheme 7). The latter result suggested that the previously discussed (Scheme 3) addition reaction to 5,6-dihydro-2H-pyran-2-one (12) might also lead to a single product if performed

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

• Markus Leibeling and
• Daniel B. Werz

Beilstein J. Org. Chem. 2013, 9, 2194–2201, doi:10.3762/bjoc.9.258

• ether should be removed by using hydrolysis and fluoride-mediated desilylation, respectively. It was assumed that the multiple carbopalladation/cyclization sequence should give access to the fourfold-annulated ring system 13 in a single step. However, we knew that the domino process works much better in

Gold catalysis for organic synthesis II

• F. Dean Toste

Beilstein J. Org. Chem. 2013, 9, 2040–2041, doi:10.3762/bjoc.9.241

• tandem or domino process that can be employed for the synthesis of complex polycyclic structures. These articles demonstrate the power of gold catalysis for the construction of complex structures, including the development of tandem processes, the expedient synthesis of heterocyclic structures, and

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

• cyclization of alkenylindoles by Pd(II) catalysis under carbonylative conditions [81][82]. This approach, based on the use of copper(II) chloride as oxidant, has been applied to 2- and 3-alkenylindoles, resulting in a domino process that involves an alkenylation/carboxylation sequence (Scheme 23). Thus

• agent in the presence of different nucleophiles suitable to generate the σ-alkyl-palladium complexes, which give the final products 54 by reductive elimination. The amide of 2-indolecarboxylic acid bearing two allylic groups (55) undergoes a domino process with generation of the tetracyclic product 56

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• different approach to α,β-alkynyl ketone derivatives as pyrazole precursors. They established a four-component domino process combining various organic halides, terminal alkynes, hydrazines, and carbon monoxide at room temperature. In this case, all components are mixed at the very beginning of the process

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

• Jonathan P. Brand,
• Clara Chevalley and
• Jérôme Waser

Beilstein J. Org. Chem. 2011, 7, 565–569, doi:10.3762/bjoc.7.65

• , step 1). Since AuCl has been shown to be the best catalyst for the alkynylation reaction [35], its use would allow a domino process with a single catalyst. Despite the fact that the use of AuCl has been reported for step 1 [19][20], in our hands the reaction was not reproducible at room temperature in

Synthesis of (–)-Indolizidine 167B based on domino hydroformylation/cyclization reactions

• Giuditta Guazzelli,
• Raffaello Lazzaroni and
• Roberta Settambolo

Beilstein J. Org. Chem. 2008, 4, No. 2, doi:10.1186/1860-5397-4-2

• heteroaromatic olefins has a topic of our research for many years [15][16][17][18][19]; now it is the first time that the rhodium catalyzed hydroformylation is employed by us in the total synthesis of a target compound and as a key reaction in a domino process with a high number of steps. Results and Discussion

• describe here a new synthesis of optically active (–)-Indolizidine 167B based on regioselective hydroformylation/intramolecular cyclization reactions which provides a general approach to the indolizine nucleus. It is a multi-step domino process which starts with the interconversion of the isomeric rhodium