Nucleophilic Sulfur Dioxide Insertion Enabled Enantioselective Michael Additions to Access α-chiral Sulfones DOI Creative Commons
Jie Wu, Xinhua Wang, Yun Mao

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 5, 2024

Abstract The asymmetric hydrosulfonylation of α,β-unsaturated carbonyls represents a significant goal in accessing α-chiral sulfones due to its high atom and step efficiency. In contrast the well-established radical sulfonylation, classical Michael addition using sulfonyl anions as nucleophiles for assembling sulfone structures remains elusive challenging. this work, we introduce first time an organocatalytic enantioselective with sulfur dioxide insertion-enabled γ-keto sulfinates nucleophiles, which provides alternative pathway producing highly enantioenriched derivatives excellent economy. methodology showcases innovative mode relay catalysis, where bifunctional organocatalyst containing both tertiary amine hydrogen bond donor sites catalyzes initial nucleophilic insertion subsequent processes two distinct manners. Mechanistic details transformation stereochemical induction were systematically verified through controlled experiments DFT calculations.

Language: Английский

Arylation of α‐Imino Ketones and their Cyclization with Allenoates: Direct Access to Sterically Hindered Pyrroles DOI Open Access
Srinivasarao Yaragorla,

Doma Arun

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Abstract Herein, we report a calcium‐catalyzed, one‐pot, four‐component reaction to synthesize diversely substituted pyrroles. This atom‐economy involves sequence of reactions that proceed via in situ formation α ‐ imino ketones, Friedel‐Crafts arylation, aza‐cyclization, and aromatization the single pot. The showed broad substrate scope with good yields. We demonstrated gram‐scale synthesis post‐synthetic modifications.

Language: Английский

Citations

1
Copper-Catalyzed Regio- and Enantioselective Protoboration of Allenyl Sulfones to Access Chiral Allylic Sulfones DOI

Peidong Sun,

Xiaomei Kong,

Huang Jing-wen

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

An efficient method for copper-catalyzed asymmetric protoboration of allenyl sulfones with bis(pinacolato)diboron was developed, providing chiral allylic high efficiency and excellent enantioselectivity. Notably, the directing effect sulfone group plays a pivotal role in achieving both regioselectivity

Language: Английский

Citations

1
Photoinduced Pd‐Catalyzed Direct Sulfonylation of Allylic C–H Bonds DOI
Vladimir Gevorgyan, Kallol Mukherjee, Kelvin Pak Shing Cheung

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)

Published: Sept. 17, 2024

Allylic sulfones are valuable motifs due to their medicinal and biological significance versatile chemical reactivities. While direct allylic C-H sulfonylation represents a straightforward desirable approach, these methods primarily restricted terminal alkenes, leaving the engagement of internal counterparts formidable challenge. Herein we report photocatalytic approach that accommodates both cyclic acyclic alkenes with diverse substitution patterns electronic properties. Importantly, obtained can be readily diversified into wide range products, thus enabling formal alkene transposition all-carbon quaternary center formation through sequential functionalization.

Language: Английский

Citations

5
Pd-Catalyzed/Ligand-Controlled Regioselective Asymmetric Hydrosulfonylation of Alkylallenes or Arylallenes DOI

Jing Wu,

Boyi Wang, Jinghan Zou

et al.

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

Published: Feb. 3, 2025

The metal-catalyzed hydrofunctionalization reaction of allenes is an efficient approach for the construction new allyl compounds. This work described a palladium-catalyzed/ligand-controlled asymmetric hydrosulfonylation simple alkylallenes and arylallenes in presence Pd2dba3. Using Josiphos or Segphos ligand, could render corresponding branched chiral allylsulfones with high yields enantioselectivities up to 90% 99% ee, respectively.

Language: Английский

Citations

0
Radical-mediated sulfonylation relay of alkyl alkynes/alkenes and electron-deficient alkenes to access vinyl and alkyl sulfones DOI
Jinhui Liu,

Fang Long,

Qing Li

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A radical-mediated sulfonylation relay of alkyl alkynes/alkenes with electron-deficient alkenes using Na 2 S O 4 as a linker is developed to synthesize highly selective ( Z )-vinyl and sulfones under metal-free catalyzed system.

Language: Английский

Citations

0
Synthesis of a sulfone-modified derivative of boron-sulphur co-doped graphitic carbon nitride photocatalyst for 1,4 NADH regeneration and synthesis of Biginelli end products DOI
Ankit Yadav, Rajesh Kumar Yadav, Kanchan Sharma

et al.

Materials Science and Engineering B, Journal Year: 2025, Volume and Issue: 318, P. 118296 - 118296

Published: April 11, 2025

Language: Английский

Citations

0
Photoinduced Pd‐Catalyzed Direct Sulfonylation of Allylic C–H Bonds DOI
Vladimir Gevorgyan, Kallol Mukherjee, Kelvin Pak Shing Cheung

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(1)

Published: Sept. 17, 2024

Abstract Allylic sulfones are valuable motifs due to their medicinal and biological significance versatile chemical reactivities. While direct allylic C−H sulfonylation represents a straightforward desirable approach, these methods primarily restricted terminal alkenes, leaving the engagement of internal counterparts formidable challenge. Herein we report photocatalytic approach that accommodates both cyclic acyclic alkenes with diverse substitution patterns electronic properties. Importantly, obtained can be readily diversified into wide range products, thus enabling formal alkene transposition all‐carbon quaternary center formation through sequential functionalization.

Language: Английский

Citations

0
Nucleophilic Sulfur Dioxide Insertion Enabled Enantioselective Michael Additions to Access α-chiral Sulfones DOI Creative Commons
Jie Wu, Xinhua Wang, Yun Mao

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 5, 2024

Abstract The asymmetric hydrosulfonylation of α,β-unsaturated carbonyls represents a significant goal in accessing α-chiral sulfones due to its high atom and step efficiency. In contrast the well-established radical sulfonylation, classical Michael addition using sulfonyl anions as nucleophiles for assembling sulfone structures remains elusive challenging. this work, we introduce first time an organocatalytic enantioselective with sulfur dioxide insertion-enabled γ-keto sulfinates nucleophiles, which provides alternative pathway producing highly enantioenriched derivatives excellent economy. methodology showcases innovative mode relay catalysis, where bifunctional organocatalyst containing both tertiary amine hydrogen bond donor sites catalyzes initial nucleophilic insertion subsequent processes two distinct manners. Mechanistic details transformation stereochemical induction were systematically verified through controlled experiments DFT calculations.

Language: Английский

Citations

0