Cleavage of carbon–carbon σ-bonds of four-membered rings

M Murakami, N Ishida - Chemical Reviews, 2020 - ACS Publications
This article reviews synthetic transformations involving cleavage of a carbon–carbon bond of
a four-membered ring, with a particular focus on the examples reported during the period …

Deconstructive synthesis of bridged and fused rings via transition-metal-catalyzed “cut-and-sew” reactions of benzocyclobutenones and cyclobutanones

Y Xue, G Dong - Accounts of Chemical Research, 2022 - ACS Publications
Conspectus Bridged and fused rings are commonly found in biologically important
molecules. Current tactics to construct these ring systems are primarily based on stepwise …

Divergent Rh Catalysis: Asymmetric Dearomatization Versus C–H Activation Initiated by C–C Activation

X Li, L Hu, S Ma, H Yu, G Lu, T Xu - ACS Catalysis, 2023 - ACS Publications
The divergent catalytic reactions based on C–C activation of benzocyclobutenones have
been discovered, consisting of a highly enantioselective dearomatic “Cut & Sew” …

Deconstructive Asymmetric Total Synthesis of Morphine‐Family Alkaloid (−)‐Thebainone A

SH Hou, AY Prichina, G Dong - … Chemie International Edition, 2021 - Wiley Online Library
Herein, we describe the development of a deconstructive strategy for the first asymmetric
synthesis of (−)‐thebainone A, capitalizing on an enantioselective C− C bond activation and …

Total Synthesis of Penicibilaenes via C–C Activation-Enabled Skeleton Deconstruction and Desaturation Relay-Mediated C–H Functionalization

Y Xue, G Dong - Journal of the American Chemical Society, 2021 - ACS Publications
Herein, we describe the first total synthesis of sesquiterpene penicibilaenes A and B through
a “C–C/C–H” approach. In the “C–C” stage, the Rh-catalyzed “cut-and-sew” transformation …

Chemo- and Diastereoselective Acylfluorination of Nonactivated Olefins to Access Benzo[b]azepines

X Liu, Y Wang, T Xu - Organic Letters, 2023 - ACS Publications
Here, we describe a transition-metal-free condition that realized the intramolecular
acylfluorination of unactivated olefins. It was designed to access seven-membered-ring …

Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+ 4] cycloaddition

J Zhang, X Wang, T Xu - Nature Communications, 2021 - nature.com
To the best of our knowledge, bridgehead carbon benzofused-bridged ring systems have
previously not been accessible to the synthetic community. Here, we describe a formal type …

Transition‐Metal‐Catalyzed Carbon‐Carbon Bond Activation in Asymmetric Synthesis

X Bi, Q Zhang, Z Gu - Chinese Journal of Chemistry, 2021 - Wiley Online Library
Catalytic asymmetric transformations involving carbon‐carbon bond cleavages open
intriguing strategies for the synthesis of chiral complex molecules. The transient …

Highly Regio- and Enantioselective Dienylation of p-Quinone Methides Enabled by an Organocatalyzed Isomerization/Addition Cascade of Allenoates

D Wang, ZF Song, WJ Wang, T Xu - Organic letters, 2019 - ACS Publications
A novel catalytic asymmetric dienylation of para-quinone methides with allenoates has been
developed. Under mild conditions catalyzed by (R)-SITCP, various dienylated …

Total synthesis of galanthamine and lycoramine featuring an early-stage C–C and a late-stage dehydrogenation via C–H activation

Y Zhang, S Shen, H Fang, T Xu - Organic letters, 2020 - ACS Publications
Herein, we report a novel strategy toward galanthamine and lycoramine. The concise
synthesis was enabled by a Rh-catalyzed gram-scale C–C activation for the tetracyclic …