Asymmetric addition of an <i>N</i>-methyl C(sp<sup>3</sup>)–H bond to cyclic alkenes enabled by an iridium/phosphine–olefin catalyst

Sakamoto, Kana; Nishimura, Takahiro

doi:10.1039/d2cc04642c

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2022

2024

Publication Types

Select...

Article3

Book2

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 5 publications

References 51 publications

(10 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

Density Functional Theory Calculations for Multiple Conformers Explaining the Regio‐ and Stereoselectivity of Ti‐Catalyzed Hydroaminoalkylation Reactions

Thoben,

Kaper,

de Graaff

et al. 2023

ChemPhysChem

View full text Add to dashboard Cite

Hybrid Density Functional Theory (DFT) calculations for multiple conformers of the insertion reactions of a methylenecyclopropane into the Ti−C bond of two differently α‐substituted titanaaziridines explain the experimentally observed differences in regioselectivity between catalytic hydroaminoalkylation reactions of methylenecyclopropanes with α‐phenyl‐substituted secondary amines and corresponding stoichiometric reactions of a methylenecyclopropane with titanaaziridines, which can only be achieved with α‐unsubstituted titanaaziridines. In addition, the lack of reactivity of α‐phenyl‐substituted titanaaziridines as well as the diastereoselectivity of the catalytic and stoichiometric reactions can be understood.

show abstract

Density Functional Theory Calculations for Multiple Conformers Explaining the Regio‐ and Stereoselectivity of Ti‐Catalyzed Hydroaminoalkylation Reactions

Thoben,

Kaper,

de Graaff

et al. 2023

ChemPhysChem

View full text Add to dashboard Cite

show abstract

Diastereoselective C–H Functionalizations

Cizikovs

Basens

Zagorska

et al. 2024

Comprehensive Chirality

View full text Add to dashboard Cite

Catalytic Addition of C–H Bonds Across C–C π-Bonds

Arribas,

Lázaro-Milla,

Mascareñas

et al. 2023

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

View full text Add to dashboard Cite

Asymmetric addition of an N-methyl C(sp³)–H bond to cyclic alkenes enabled by an iridium/phosphine–olefin catalyst

Abstract: Iridium-catalyzed asymmetric C–H addition of an N-methy group on 3-trifluoromethyl-2-(N-methylamino)pyridine to cyclic alkenes was realized by using a phosphine-olefin ligand. Indene and its 7-substituted derivatives, acenaphthylene, and some bicyclic alkenes...

Cited by 5 publications

References 51 publications

Density Functional Theory Calculations for Multiple Conformers Explaining the Regio‐ and Stereoselectivity of Ti‐Catalyzed Hydroaminoalkylation Reactions

Density Functional Theory Calculations for Multiple Conformers Explaining the Regio‐ and Stereoselectivity of Ti‐Catalyzed Hydroaminoalkylation Reactions

Diastereoselective C–H Functionalizations

Catalytic Addition of C–H Bonds Across C–C π-Bonds

Contact Info

Product

Resources

About

Asymmetric addition of an N-methyl C(sp3)–H bond to cyclic alkenes enabled by an iridium/phosphine–olefin catalyst

Abstract: Iridium-catalyzed asymmetric C–H addition of an N-methy group on 3-trifluoromethyl-2-(N-methylamino)pyridine to cyclic alkenes was realized by using a phosphine-olefin ligand. Indene and its 7-substituted derivatives, acenaphthylene, and some bicyclic alkenes...

Cited by 5 publications

References 51 publications

Density Functional Theory Calculations for Multiple Conformers Explaining the Regio‐ and Stereoselectivity of Ti‐Catalyzed Hydroaminoalkylation Reactions

Density Functional Theory Calculations for Multiple Conformers Explaining the Regio‐ and Stereoselectivity of Ti‐Catalyzed Hydroaminoalkylation Reactions

Diastereoselective C–H Functionalizations

Catalytic Addition of C–H Bonds Across C–C π-Bonds

Contact Info

Product

Resources

About

Asymmetric addition of an N-methyl C(sp³)–H bond to cyclic alkenes enabled by an iridium/phosphine–olefin catalyst