Expedient (3+3)-annulation of carbonyl ylides with azaoxyallyl cations: formal access to oxa-benzo[c]azepin-3-ones DOI
Kshitiz Verma, Hemanga Bhattacharyya, Sharajit Saha

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Cascade C–C/C–N bond formation of carbonyl ylides with azaoxyallyl cations generated in situ using Rh-catalysis has been accomplished the presence a base at room temperature.

Language: Английский

Visible-Light-Induced [4 + 3]-Annulation of Carbonyl Ylides with Alkenyl Pyrazolinone for Constructing [4.2.1]-Oxo-Bridged Oxocine Skeleton DOI

Dong-Sheng Ji,

Xin Zhang,

Peiqin Zhang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 709 - 714

Published: Jan. 7, 2025

Herein, we present a visible-light-induced protocol for the synthesis of highly functionalized oxo-bridged oxocine skeletons. This method generates carbenes via ortho-acyl diazo compounds, which are rapidly intercepted by oxygen atom an intermolecular acyl group to form cyclic 1,3-dipole. The in situ generated reactive 1,3-dipole undergoes facile formal [4 + 3] cycloaddition with alkenyl pyrazolinone, yielding [4.2.1]-oxo-bridged compounds.

Language: Английский

Citations

2
Stereoselective (3 + 3)-Cycloannulation of Carbonyl Ylides and (Z)-3-Benzylidene-3H-indoles Enabled by Cooperative Rh/Chiral Phosphoric Acid Catalysis DOI

Jharna Barman,

S. Ananda,

Subhas Chandra Pan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 19, 2025

A diastereo- and enantioselective (3 + 3)-cycloannulation of in situ generated carbonyl ylides (Z)-3-benzylidene-3H-indoles enabled by cooperative Rh/chiral phosphoric acid catalysis is reported. This study the first to describe an synthesis cyclohepta[b]indole with oxa-bridged motif. The scope reaction broad, products were obtained moderate good yields excellent diastereoselectivities high enantioselectivities.

Language: Английский

Citations

0
Three-Component 1,3-Difunctionalization of Carbonyl Ylides with Water and Azadienes for the Synthesis of Dihydroisobenzofurans DOI
Haiqing Wang,

Yunzhe Wang,

Jie Ren

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Multicomponent reactions are an efficient and widely employed synthetic strategy, known for their capability to rapidly effectively construct complex molecular architectures from multiple starting materials. This work presents a chemo- diastereoselective three-component reaction the 1,3-difunctionalization of transient carbonyl ylides with H2O azadienes, facilitated by synergistic catalysis Rh2(OAc)4 phosphoric acid. strategy provides protocol synthesis highly functionalized dihydroisobenzofurans in high yields (up 94%) good diastereoselectivities 91:9 dr). Additionally, subsequent transformations nucleophiles enable structurally diverse compounds enhanced (dr >95:5).

Language: Английский

Citations

0
Sc(OTf)3-Catalyzed Precise Construction of Medium-Sized [4.2.1]-Oxabridged Scaffolds DOI

Dong-Sheng Ji,

Chenxing Zhou,

Xudong Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

In this study, the readily available and inexpensive Sc(OTf)

Language: Английский

Citations

2
Expedient (3+3)-annulation of carbonyl ylides with azaoxyallyl cations: formal access to oxa-benzo[c]azepin-3-ones DOI
Kshitiz Verma, Hemanga Bhattacharyya, Sharajit Saha

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Cascade C–C/C–N bond formation of carbonyl ylides with azaoxyallyl cations generated in situ using Rh-catalysis has been accomplished the presence a base at room temperature.

Language: Английский

Citations

1