One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives DOI

Zefeng Jin,

LI Cui-ying,

Guodong Shen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(24), P. 5151 - 5159

Published: Aug. 29, 2024

Abstract A copper or silver‐catalyzed cascade addition/5‐ exo‐dig cyclization/isomerization reaction of isothiocyanate with ynone has been developed. This strategy enables the synthesis a variety ( Z )‐2‐ylidene‐5‐aminothiophen‐3‐one derivatives diverse substitutions in single vessel. The method is featured pot‐economy as well regio‐ and ‐selectivity. Several biologically active molecules could be modified using this strategy. Moreover, relevant indole‐fused indole‐substituted thiophenone were also assembled one pot by merging other bond formation methods. Based on experiments related reports, pathway triggered addition ynone‐derived radical towards C( sp )‐atom was proposed to elucidate probable process transformation.

Language: Английский

Catalytic Asymmetric Barbier Reaction of Ketones with Unactivated Alkyl Electrophiles DOI

Hanyu Xia,

Xingni Jiang,

Di Lin

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 3, 2024

The Barbier reaction is a reductive-type addition of an aldehyde or ketone with organic electrophile in the presence terminal metal reductant, providing straightforward and efficient method for carbon-carbon bond formation. This possesses advantage circumventing preparation moisture- air-sensitive organometallic reagents. However, catalytic ketones to construct tetrasubstituted stereogenic centers largely underdeveloped, despite its great potential accessing synthetically challenging chiral tertiary alcohol. Particularly, leveraging unactivated alkyl electrophiles as coupling components still rarely exploited. Herein, we disclose photoredox-assisted cobalt-catalyzed asymmetric alkylative Barbier-type address aforementioned challenges, thereby allowing construction highly congested carbon centers. fragments could be either readily accessible halides redox-active esters generated through decarboxylative pathway. Both types include primary, secondary, ones, thus affording diverse enantioenriched alcohols broad substrate scope. enantioselective protocol applied expedient synthesis core structure

Language: Английский

Citations

2

Cobalt-Catalyzed Enantioselective Reductive Addition of Ketimine with Cyclopropyl Chloride to Construct the Chiral Amino Esters Bearing Cyclopropyl Fragments DOI
Jiangtao Hu, Tingting Xia, Xianqing Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(22), P. 6311 - 6318

Published: Jan. 1, 2024

Co-catalyzed asymmetric reductive addition of ketimine with cyclopropyl chloride has been realized to access diverse chiral amino esters bearing fragments broad functional group tolerance and excellent enantioselectivities.

Language: Английский

Citations

1

Synthesis of β-Tertiary Amino Acids Analogues via Cobalt-Catalyzed Stereoselective Radical Addition DOI
Hisashi Yamamoto, Abhijit Paul

Synfacts, Journal Year: 2024, Volume and Issue: 20(05), P. 0553 - 0553

Published: April 15, 2024

Key words β-tertiary amino acids - asymmetric reductive addition radical pathway

Language: Английский

Citations

0

One‐Pot Reactions of Ynones with Isothiocyanates for Accessing 2‐Aminothiophenone and Indole‐Fused/Indole‐Substituted Thiophenone Derivatives DOI

Zefeng Jin,

LI Cui-ying,

Guodong Shen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(24), P. 5151 - 5159

Published: Aug. 29, 2024

Abstract A copper or silver‐catalyzed cascade addition/5‐ exo‐dig cyclization/isomerization reaction of isothiocyanate with ynone has been developed. This strategy enables the synthesis a variety ( Z )‐2‐ylidene‐5‐aminothiophen‐3‐one derivatives diverse substitutions in single vessel. The method is featured pot‐economy as well regio‐ and ‐selectivity. Several biologically active molecules could be modified using this strategy. Moreover, relevant indole‐fused indole‐substituted thiophenone were also assembled one pot by merging other bond formation methods. Based on experiments related reports, pathway triggered addition ynone‐derived radical towards C( sp )‐atom was proposed to elucidate probable process transformation.

Language: Английский

Citations

0