Development of Organocatalytic Darzens Reactions Exploiting the Cyclopropenimine Superbase DOI Creative Commons

Carmine Lops,

Lucia Pasquato, Paolo Pengo

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(18), P. 4350 - 4350

Published: Sept. 13, 2024

A truly organocatalytic approach to the Darzens reaction affording

Language: Английский

Enantioselective dearomative formal (3+3) cycloadditions of bicyclobutanes with aromatic azomethine imines: access to fused 2,3-diazabicyclo[3.1.1]heptanes DOI Creative Commons
Xue-Chun Yang, Feng Wu, Wen‐Biao Wu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(46), P. 19488 - 19495

Published: Jan. 1, 2024

We present the first enantioselective dearomative (3+3) cycloadditions of bicyclobutanes (BCBs) utilizing a chiral Lewis acid catalyst and bidentate chelating BCB substrates.

Language: Английский

Citations

5
Copper(II)-Catalyzed Asymmetric (3+3) Annulation of Diaziridines with Oxiranes DOI
Ying Hu,

Heng-Bin Yu,

Tian Yin

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(5), P. 1310 - 1315

Published: Jan. 29, 2025

Highly asymmetric (3+3) annulation of diaziridines with oxiranes via C-N bond cleavage in diaziridine was achieved under 10 mol % chiral copper(II) complex as the catalyst mild reaction conditions. With Cu(OTf)2 Lewis acid and C1-symmetric imidazolidine-pyrroloimidazolone pyridine ligand, diverse tetrahydro-[1,3,4]-oxadiazines were obtained by stereospecific C-N/C-O formation moderate to good yields (up 93% yield) high diastereo- (>20:1 dr) enantioselectivities 92% ee). The catalytic cycle stereochemical model proposed DFT calculation.

Language: Английский

Citations

0
Chemoselectivity Switch between Enantioselective [2,3]‐Wittig Rearrangement and Conia‐Ene‐Type Reactions of Propargyloxyoxindoles DOI
Yulin Gao, Yang Yang, Chen Wu

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 25, 2024

Abstract Despite the existence of three competing reactions for propargyloxyoxindoles, we report a chemoselectivity switch between enantioselective propargyl [2,3]‐Wittig rearrangement and Conia‐ene‐type reactions, with suppression [1,2]‐Wittig‐type rearrangement. Using C 1 ‐symmetric imidazolidine‐pyrroloimidazolone pyridine as ligand Ni(acac) 2 Lewis acid, diverse 3‐hydroxy 3‐substituted oxindoles containing allenyl groups were obtained in up to 98 % yield 99 ee via asymmetric In presence AgOTf‐Duanphos, chiral spiro dihydrofuran given 91 through reaction.

Language: Английский

Citations

0
Development of Organocatalytic Darzens Reactions Exploiting the Cyclopropenimine Superbase DOI Creative Commons

Carmine Lops,

Lucia Pasquato, Paolo Pengo

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(18), P. 4350 - 4350

Published: Sept. 13, 2024

A truly organocatalytic approach to the Darzens reaction affording

Language: Английский

Citations

0