Side-Arm-Promoted Highly Enantioselective Ring-Opening Reactions and Kinetic Resolution of Donor–Acceptor Cyclopropanes with Amines

2012 ◽  
Vol 134 (22) ◽  
pp. 9066-9069 ◽  
Author(s):  
You-Yun Zhou ◽  
Li-Jia Wang ◽  
Jun Li ◽  
Xiu-Li Sun ◽  
Yong Tang
Keyword(s):  
Ring Opening ◽  
Kinetic Resolution ◽  
Ring Opening Reactions ◽  
Donor Acceptor

Ring-opening reactions of donor–acceptor cyclopropanes with cyclic ketals and thiol ketals

2020 ◽  
Vol 18 (33) ◽  
pp. 6492-6496 ◽  
Author(s):  
Dongxin Zhang ◽  
Lei Yin ◽  
Junchao Zhong ◽  
Qihang Cheng ◽  
Hu Cai ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Donor Acceptor

Cyclic (thiol) ketals were used as hetero-nucleophiles for the ring opening of donor–acceptor cyclopropanes to afford functionalized diethers.

Catalytic Asymmetric Transformations of Racemic Aziridines

Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1738-1750 ◽  
Author(s):  
Zhuo Chai
Keyword(s):  
Ring Opening ◽  
Kinetic Resolution ◽  
Short Review ◽  
Asymmetric Transformations ◽  
Parallel Kinetic Resolution ◽  
Donor Acceptor ◽  
Molecular Architectures ◽  
Catalytic Asymmetric ◽  
Asymmetric Transformation ◽  
Asymmetric Ring Opening

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.1 Introduction2 Reaction of Racemic 2-Vinylaziridines3 Reaction of Racemic 2-Alkylaziridines3.1 Regiodivergent Parallel Kinetic Resolution3.2 Kinetic Resolution4 Reaction of Racemic 2-(Hetero)arylaziridines4.1 Kinetic Resolution4.2 Enantioconvergent Transformation5 Reaction of Racemic Donor–Acceptor-Type Aziridines6 Conclusion and Outlook

scholarly journals Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3035-3068 ◽  
Author(s):  
Ekaterina Budynina ◽  
Konstantin Ivanov ◽  
Ivan Sorokin ◽  
Mikhail Melnikov
Keyword(s):  
Ring Opening ◽  
Building Blocks ◽  
Simple Approach ◽  
Secondary Amines ◽  
Primary Amines ◽  
Pyrrole Derivatives ◽  
Heteroaromatic Compounds ◽  
Azide Ion ◽  
Ring Opening Reactions ◽  
Donor Acceptor

Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.1 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary

Ring-opening reactions of cyclopropanes. Part 8.1 Nitrosation of donor–acceptor cyclopropanes

2005 ◽  
Vol 2005 (10) ◽  
pp. 677-681 ◽  
Author(s):  
Flavio Cermola ◽  
Lucrezia Di Gioia ◽  
Maria Liliana Graziano ◽  
Maria Rosaria Iesce
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Donor Acceptor

The reaction of 2,2-dialkoxycyclopropane-1-carboxylates 1a–d and monoalkoxycyclopropane 1e with NOCl gives isoxazoline- and/or isoxazole-3-carboxylates by regioselective ring-opening at C1–C2 bond. A mechanistic interpretation suggests the intermediacy of well-stabilised dipolar species.

DBU-promoted ring-opening reactions of multi-substituted donor–acceptor cyclopropanes: access to functionalized chalcones with a quaternary carbon group

2020 ◽  
Vol 18 (45) ◽  
pp. 9210-9215
Author(s):  
Naili Luo ◽  
Jiamin Liu ◽  
Shan Wang ◽  
Cunde Wang
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Metal Catalyst ◽  
Quaternary Carbon ◽  
Transition Metal Catalyst ◽  
Ring Opening Reactions ◽  
Donor Acceptor

A strategy to synthesize highly stereoselective chalcones with alkylcyanoacetate subunits via DBU-promoted ring-opening reactions of multi-substituted D–A cyclopropanes has been developed without the requirement of a transition metal catalyst and extra solvent.

Ring-Opening Reactions of Donor–Acceptor Cyclobutanes with Electron-Rich Arenes, Thiols, and Selenols

2019 ◽  
Vol 21 (16) ◽  
pp. 6315-6319 ◽  
Author(s):  
Alexander Kreft ◽  
Stephanie Ehlers ◽  
Peter G. Jones ◽  
Daniel B. Werz
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Donor Acceptor
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