Copper‐Catalyzed Asymmetric Radical 1,2‐Alkylesterification of 1,3‐Dienes with Cycloalkyl Hydroperoxides and Acids DOI
Tiantian Li, Ying Cheng, Wen‐Jing Xiao

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(23)

Published: Oct. 17, 2023

Abstract Transition‐metal‐catalyzed radical relay cross‐coupling reactions of 1,3‐dienes have recently emerged as one the most powerful methods for construction structurally diverse allylic compound in a single chemical step. However, there still has been limited success expanding substrate scope precursors and coupling partners, well exploring catalytic asymmetric variants. Herein, we report copper‐catalyzed enantioselective three‐component 1,2‐alkylesterification using cycloalkyl hydroperoxides carbonyl‐containing alkyl sources carboxylic acids O‐nucleophiles under mild redox‐neutral conditions. This protocol features broad good functional group tolerance with respect to each component, providing practical access variety distally keto‐functionalized esters high enantioselectivity. Mechanistic studies suggest involvement sequential C−O this reaction.

Language: Английский

When all C–C breaks LO–Ose DOI Creative Commons

Jeremy H. Dworkin,

Brady W. Dehnert,

Ohyun Kwon

et al.

Trends in Chemistry, Journal Year: 2023, Volume and Issue: 5(3), P. 174 - 200

Published: Feb. 14, 2023

Organic peroxides are becoming popular intermediates for novel chemical transformations. The weak O-O bond is readily reduced by transition metals, including iron and copper, to initiate a radical cascade process that breaks C-C bonds. Great potential exists the rapid generation of complexity, originating from ability couple resulting free radicals with wide range partners. First, this review article discusses history synthesis organic peroxides, providing context necessary understand methodology. Then, it highlights 91 examples recent applications functionalization bonds accessed through metal-mediated reduction peroxides. Finally, we provide some comments about safety when working

Language: Английский

Citations

18
Copper‐Catalyzed Asymmetric Radical 1,2‐Alkylesterification of 1,3‐Dienes with Cycloalkyl Hydroperoxides and Acids DOI
Tiantian Li, Ying Cheng, Wen‐Jing Xiao

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(23)

Published: Oct. 17, 2023

Abstract Transition‐metal‐catalyzed radical relay cross‐coupling reactions of 1,3‐dienes have recently emerged as one the most powerful methods for construction structurally diverse allylic compound in a single chemical step. However, there still has been limited success expanding substrate scope precursors and coupling partners, well exploring catalytic asymmetric variants. Herein, we report copper‐catalyzed enantioselective three‐component 1,2‐alkylesterification using cycloalkyl hydroperoxides carbonyl‐containing alkyl sources carboxylic acids O‐nucleophiles under mild redox‐neutral conditions. This protocol features broad good functional group tolerance with respect to each component, providing practical access variety distally keto‐functionalized esters high enantioselectivity. Mechanistic studies suggest involvement sequential C−O this reaction.

Language: Английский

Citations

6