α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene CatalystsCitation formats

  • External authors:
  • David P. Tilly
  • William Cullen
  • Heng Zhong
  • Romain Jamagne
  • Inigo Vitórica‐yrezábal

Standard

α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene Catalysts. / Tilly, David P.; Cullen, William; Zhong, Heng et al.

In: Chemistry – A European Journal, 12.01.2022.

Research output: Contribution to journalArticlepeer-review

Harvard

Tilly, DP, Cullen, W, Zhong, H, Jamagne, R, Vitórica‐yrezábal, I & Webb, SJ 2022, 'α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene Catalysts', Chemistry – A European Journal. https://doi.org/10.1002/chem.202104293

APA

Tilly, D. P., Cullen, W., Zhong, H., Jamagne, R., Vitórica‐yrezábal, I., & Webb, S. J. (2022). α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene Catalysts. Chemistry – A European Journal. https://doi.org/10.1002/chem.202104293

Vancouver

Tilly DP, Cullen W, Zhong H, Jamagne R, Vitórica‐yrezábal I, Webb SJ. α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene Catalysts. Chemistry – A European Journal. 2022 Jan 12. https://doi.org/10.1002/chem.202104293

Author

Tilly, David P. ; Cullen, William ; Zhong, Heng et al. / α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene Catalysts. In: Chemistry – A European Journal. 2022.

Bibtex

@article{6ccbc4c2c79948e78d48779e33444174,
title = "α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene Catalysts",
abstract = "To investigate how remotely induced changes in ligand folding might affect catalysis by organometallic complexes, dynamic α-amino-iso-butyric acid (Aib) peptide foldamers bearing rhodium(I) N-heterocyclic carbene (NHC) complexes have been synthesised and studied. X-ray crystallography of a foldamer with an N-terminal azide and a C-terminal Rh(NHC)(Cl)(diene) complex showed a racemate with a chiral axis in the Rh(NHC) complex and a distorted 310 helical body. Replacing the azide with either one or two chiral Lα-methylvaline (L-αMeVal) residues gave diastereoisomeric foldamers that each possessed point, helical and axial chirality. NMR spectroscopy revealed an unequal ratio of diastereoisomers for some foldamers, indicating that the chiral conformational preference of the N-terminal residue(s) was relayed down the 1 nm helical body to the axially chiral Rh(NHC) complex. Although the remote chiral residue(s) did not affect the stereoselectivity of hydrosilylation reactions catalysed by these foldamers, these studies suggest a potential pathway towards remote conformational control of organometallic catalysts.",
author = "Tilly, {David P.} and William Cullen and Heng Zhong and Romain Jamagne and Inigo Vit{\'o}rica‐yrez{\'a}bal and Webb, {Simon J.}",
year = "2022",
month = jan,
day = "12",
doi = "10.1002/chem.202104293",
language = "English",
journal = "Chemistry: A European Journal ",
issn = "0947-6539",
publisher = "John Wiley & Sons Ltd",

}

RIS

TY - JOUR

T1 - α‐Amino‐iso‐Butyric Acid Foldamers Terminated with Rhodium(I) N‐Heterocyclic Carbene Catalysts

AU - Tilly, David P.

AU - Cullen, William

AU - Zhong, Heng

AU - Jamagne, Romain

AU - Vitórica‐yrezábal, Inigo

AU - Webb, Simon J.

PY - 2022/1/12

Y1 - 2022/1/12

N2 - To investigate how remotely induced changes in ligand folding might affect catalysis by organometallic complexes, dynamic α-amino-iso-butyric acid (Aib) peptide foldamers bearing rhodium(I) N-heterocyclic carbene (NHC) complexes have been synthesised and studied. X-ray crystallography of a foldamer with an N-terminal azide and a C-terminal Rh(NHC)(Cl)(diene) complex showed a racemate with a chiral axis in the Rh(NHC) complex and a distorted 310 helical body. Replacing the azide with either one or two chiral Lα-methylvaline (L-αMeVal) residues gave diastereoisomeric foldamers that each possessed point, helical and axial chirality. NMR spectroscopy revealed an unequal ratio of diastereoisomers for some foldamers, indicating that the chiral conformational preference of the N-terminal residue(s) was relayed down the 1 nm helical body to the axially chiral Rh(NHC) complex. Although the remote chiral residue(s) did not affect the stereoselectivity of hydrosilylation reactions catalysed by these foldamers, these studies suggest a potential pathway towards remote conformational control of organometallic catalysts.

AB - To investigate how remotely induced changes in ligand folding might affect catalysis by organometallic complexes, dynamic α-amino-iso-butyric acid (Aib) peptide foldamers bearing rhodium(I) N-heterocyclic carbene (NHC) complexes have been synthesised and studied. X-ray crystallography of a foldamer with an N-terminal azide and a C-terminal Rh(NHC)(Cl)(diene) complex showed a racemate with a chiral axis in the Rh(NHC) complex and a distorted 310 helical body. Replacing the azide with either one or two chiral Lα-methylvaline (L-αMeVal) residues gave diastereoisomeric foldamers that each possessed point, helical and axial chirality. NMR spectroscopy revealed an unequal ratio of diastereoisomers for some foldamers, indicating that the chiral conformational preference of the N-terminal residue(s) was relayed down the 1 nm helical body to the axially chiral Rh(NHC) complex. Although the remote chiral residue(s) did not affect the stereoselectivity of hydrosilylation reactions catalysed by these foldamers, these studies suggest a potential pathway towards remote conformational control of organometallic catalysts.

U2 - 10.1002/chem.202104293

DO - 10.1002/chem.202104293

M3 - Article

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

ER -