Synthesis of heterocycles based on azomethine ylides from α-amino acids (or amines) and carbonyl compounds

• Ekaterina V. Berezhnaya,
• Alexander I. Ponyaev,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2026, 22, 705–741, doi:10.3762/bjoc.22.55

• aromatic ring, as well as heterosubstituted alkenes and polyenes, are also known [30][31][32]. The review [33] examines the reactions of 1,3-dipolar cycloaddition of cyclopropenes with various dipoles, such as diazo compounds, azides, azomethine imines, nitrones, azomethine ylides, carbonyl ylides, etc. At

One-pot synthesis of epoxides from benzyl alcohols and aldehydes

• Edwin Alfonzo,
• Jesse W. L. Mendoza and
• Aaron B. Beeler

Beilstein J. Org. Chem. 2018, 14, 2308–2312, doi:10.3762/bjoc.14.205

• into carbonyls [8][9][10][11][12][13][14][15][16][17], and application to cascade or domino reactions [18][19]. More recently, our group has used benzyl epoxides for the photoredox generation of carbonyl ylides which are leveraged in the synthesis of cyclic ethers [20]. This work has led us to search

Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis

• Anna Kuźnik,
• Roman Mazurkiewicz and
• Beata Fryczkowska

Beilstein J. Org. Chem. 2017, 13, 2710–2738, doi:10.3762/bjoc.13.269

• imidoylation of β-carbonyl ylides: 2-(N-Acylamino)vinylphosphonium halides 22 can be prepared by imidoylation of β-carbonyl phosphorus ylides with imidoyl halides in acetonitrile (Scheme 15). The obtained salts 22 are stable, crystalline compounds that are usually synthesized in good yields according to one of

• addition of triphenylphosphine to acetylenedicarboxylates in the presence of nucleophiles. Synthesis of 2-(N-acylamino)vinylphosphonium halides by imidoylation of β-carbonyl ylides with imidoyl halides. Imidoylation of β-carbonyl ylides with imidoyl halides generated in situ. Synthesis of 2

Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4-phthalimidocarboxylic esters derived from methionine and cysteine

• Marc Enßle,
• Stefan Buck,
• Roland Werz and
• Gerhard Maas

Beilstein J. Org. Chem. 2012, 8, 433–440, doi:10.3762/bjoc.8.49

• rearrangement. The short-lived carbonyl ylides derived from methionine and S-benzylcysteine formed head-to-tail dimers by a [3 + 3]-cycloaddition and could be trapped with external dipolarophiles, while the S-allyl derivative 14c yielded the pentacyclic compound 17 by an intramolecular [3 + 2]-cycloaddition

• reaction. Keywords: α-aminoacids; carbonyl ylides; cycloaddition; α-diazo-β-ketoesters; sulfonium ylides; Introduction The synthetic potential of diazo compounds, in particular of α-diazoketones and α-diazoesters, is greatly widened by the ability of the derived carbene or metal-carbene intermediates to

• , yielding either a cyclic sulfonium ylide or a six-ring carbonyl ylide. In fact, it has been found that Rh(II)-catalyzed dediazoniation of α-diazo-β-ketoesters with γ-phthalimido [18][19] or related [20] substituents gives rise to cyclic carbonyl ylides, which were trapped by intermolecular cycloaddition