Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173
Published: Jan. 1, 2024
Language: Английский
Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141768 - 141768
Published: Feb. 1, 2025
Language: Английский
Citations
1
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(19), P. 14177 - 14182
Published: Sept. 18, 2024
An approach involving the use of a bifunctional aminocatalyst containing Brønsted base and iminium activation sites for asymmetric multicomponent reactions [1,2]-phospha-Brook rearrangement has yet to be realized. Herein, we present an aminocatalytic enantioselective conjugate addition α-phosphonyloxy enolates formed
Language: Английский
Citations
4
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1857 - 1862
Published: Feb. 21, 2024
Abstract An intermolecular addition reaction involving an unconventional combination of a diarylmethyl anion and electrophile, which is mediated by the [1,2]‐phospha‐Brook rearrangement under Brønsted base catalysis, was developed. Diarylmethyl anions having benzofuran moiety were generated through with aid catalytic amount phosphazene P2‐ t Bu. The resulting carbanion intermediates trapped various electrophiles, such as α,β‐unsaturated ketones, aryl aldehydes, α‐ketoesters, N ‐Boc imines, providing corresponding diarylalkane derivatives in good yields.
Language: Английский
Citations
3
ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(35), P. 13336 - 13351
Published: Aug. 22, 2024
An environmentally friendly multicomponent reaction strategy for the synthesis of functionally rich all-carbon substituted 2,3-dihydro-1H-pyrrol-2-ols "in-water" at room temperature has been reported. Water plays an indispensable role in presence readily available catalytic surfactants sodium dioctylsulfosuccinate and dodecyl sulfate to effectuate transformation, as proved by inferior results obtained organic solvents. A wide display substrate scope functional group compatibility permits diversity generation a mild operationally simple fashion. High product yields, fast rate, recoverability/recyclability catalysts, high TON/TOF, ease purification final products filtration, AE values, excellent E-factor count with score low possible highlight "greenness" this approach. Feasibility "gram-scale" synthetic elaboration offer notable advantages. The mechanistic understanding intercepting labile "imine" intermediate realized through sequence imine formation Mannich-type followed intramolecular N-cyclization.
Language: Английский
Citations
3
International Journal of Molecular Sciences, Journal Year: 2025, Volume and Issue: 26(7), P. 3065 - 3065
Published: March 27, 2025
The [1,2]-phospha-Brook rearrangement serves as a powerful synthetic strategy that enables efficient carbonyl umpolung through phosphoryl group migration, providing direct access to α-hydroxyphosphoryl compounds-a privileged class of synthons with broad applications in organophosphorus chemistry, medicinal and materials science. This review provides comprehensive overview recent progress methodologies, possible mechanisms, asymmetric transformations, highlighting key breakthroughs future directions this rapidly evolving field.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: May 1, 2025
A highly efficient and stereoselective [1,2]-phospha-Brook rearrangement of fluoromethyl ketones has been achieved by utilizing a new type P-chiral H-phosphonate derived from CAMDOL, designated as CAMDOL-PHO. library 38 secondary alcohols featuring an α-trifluoromethyl or trifluoroaryl motif were afforded in up to 97% yield with 99:1 dr. Compared other known chiral auxiliaries, bicyclic CAMDOL exhibits superior induction ability due its unique center-chiral scaffold.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: May 2, 2025
An asymmetric catalytic Pudovik addition/[1,2]-phospha-Brook rearrangement/allylation reaction of readily available isatins, phosphites, and vinyl ethylene carbonate enabled by a chiral iridium catalyst was developed in one-pot fashion. A wide range enantioenriched oxindole derivatives containing two adjacent stereocenters could be obtained good to high yields with excellent diastereoselectivity enantioselectivity (65-99% yield, 7:1 >20:1 dr, generally 99% ee). This cascade protocol owned the advantages starting materials, regio-/diastereo-/enantioselectivity, substrate scope generality.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: May 14, 2025
The ideal deuteration, for organic synthetic chemists, might include the use of a cheap deuterium source, mild operating conditions, and diverse transformations. We developed an umpolung sequence reductive deuteration aldehydes/ketones, affording synthetically useful monodeuterated phosphinates. further one-pot transformation plausible mechanism this reaction were studied.
Language: Английский
Citations
0
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 14058 - 14068
Published: Sept. 10, 2024
Language: Английский
Citations
2
Acta Chimica Sinica, Journal Year: 2024, Volume and Issue: 82(2), P. 119 - 119
Published: Jan. 1, 2024
Language: Английский
Citations
1