Copper‐Catalyzed Enantioselective Doyle–Kirmse Reaction of Azide‐Ynamides via α‐Imino Copper Carbenes DOI
Xin Liu, Li‐Gao Liu,

Can‐Ming Chen

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(10)

Published: Jan. 14, 2023

Abstract [2,3]‐Sigmatropic rearrangement reaction involving sulfonium ylide (Doyle–Kirmse reaction) generated from metal carbenes represents one of the powerful methods for construction C(sp 3 )−S and C−C bonds. Although significant advances have been achieved, asymmetric versions via generation ylides rarely reported to date, they so far limited diazo compounds as carbene precursors. Here, we describe a copper‐catalyzed enantioselective Doyle–Kirmse azide‐ynamide cyclization, leading practical divergent assembly an array chiral [1,4]thiazino[3,2‐ b ]indoles bearing quaternary carbon stereocenter in generally moderate excellent yields enantioselectivities. Importantly, this protocol unique catalytic non‐diazo approach unprecedented [2,3]‐sigmatropic α‐imino carbenes.

Language: Английский

Copper‐Catalyzed Enantioselective Doyle–Kirmse Reaction of Azide‐Ynamides via α‐Imino Copper Carbenes DOI
Xin Liu, Li‐Gao Liu,

Can‐Ming Chen

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(10)

Published: Jan. 14, 2023

[2,3]-Sigmatropic rearrangement reaction involving sulfonium ylide (Doyle-Kirmse reaction) generated from metal carbenes represents one of the powerful methods for construction C(sp3 )-S and C-C bonds. Although significant advances have been achieved, asymmetric versions via generation ylides rarely reported to date, they so far limited diazo compounds as carbene precursors. Here, we describe a copper-catalyzed enantioselective Doyle-Kirmse azide-ynamide cyclization, leading practical divergent assembly an array chiral [1,4]thiazino[3,2-b]indoles bearing quaternary carbon stereocenter in generally moderate excellent yields enantioselectivities. Importantly, this protocol unique catalytic non-diazo approach unprecedented [2,3]-sigmatropic α-imino carbenes.

Language: Английский

Citations

30
Efficient Accessibility of Indole and Pyrrole Nuclei via Late-Stage Aryl C-H Activation of Drug Molecules Promoted by Thianthrenium Salts DOI

Wangcheng Hu,

Tingting Yang, Shuguang Chen

et al.

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

Published: Jan. 1, 2024

An efficient redox-neutral palladium-catalyzed system has been developed to introduce indole and pyrrole various bioactive molecules via late-stage aryl C–H activation, providing a robust tool explore structure–activity relationships (SARs).

Language: Английский

Citations

0
Copper‐Catalyzed Enantioselective Doyle–Kirmse Reaction of Azide‐Ynamides via α‐Imino Copper Carbenes DOI
Xin Liu, Li‐Gao Liu,

Can‐Ming Chen

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(10)

Published: Jan. 14, 2023

Abstract [2,3]‐Sigmatropic rearrangement reaction involving sulfonium ylide (Doyle–Kirmse reaction) generated from metal carbenes represents one of the powerful methods for construction C(sp 3 )−S and C−C bonds. Although significant advances have been achieved, asymmetric versions via generation ylides rarely reported to date, they so far limited diazo compounds as carbene precursors. Here, we describe a copper‐catalyzed enantioselective Doyle–Kirmse azide‐ynamide cyclization, leading practical divergent assembly an array chiral [1,4]thiazino[3,2‐ b ]indoles bearing quaternary carbon stereocenter in generally moderate excellent yields enantioselectivities. Importantly, this protocol unique catalytic non‐diazo approach unprecedented [2,3]‐sigmatropic α‐imino carbenes.

Language: Английский

Citations

0