Pd-catalyzed carbonylative alpha-arylation of azlactones: A formal four-component coupling route to alpha,alpha-disubstituted amino acids

Danielle Lobo Just Pinheiro; Dennis Ulsøe Nielsen; Giovanni Amarante; Troels Skrydstrup

doi:10.1016/j.jcat.2018.04.027

Pd-catalyzed carbonylative alpha-arylation of azlactones: A formal four-component coupling route to alpha,alpha-disubstituted amino acids

Danielle Lobo Just Pinheiro
, Dennis Ulsøe Nielsen
, Giovanni Amarante
, Troels Skrydstrup

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

10 Citations (Scopus)

Abstract

We report on a Pd-catalyzed carbonylative α-arylation of azlactones derived from alanine, providing facile access to α,α-disubstituted amino acids after an alcoholysis step. A range of aryl iodides proved to be suitable substrates in this formal four-component approach, providing the desired products in good to high yields. Other amino acids, such as methionine, leucine and phenylalanine could be functionalized in a similar manner with this methodology. The possibility for isotope labeling ( ¹³C, ²H) was demonstrated, as well as chemoselective transformations of the tricarbonyl-containing molecules.

Original language	English
Journal	Journal of Catalysis
Volume	364
Pages (from-to)	366–370
Number of pages	5
ISSN	0021-9517
DOIs	https://doi.org/10.1016/j.jcat.2018.04.027
Publication status	Published - Aug 2018

Keywords

Amino acids
Azlactones
Carbon monoxide
Catalysis
Palladium

Access to Document

10.1016/j.jcat.2018.04.027

Library access?

Check availability with the Royal Danish Library

Cite this

@article{bd715bc073bf4eb5bf47494b2cbcd58e,

title = "Pd-catalyzed carbonylative alpha-arylation of azlactones: A formal four-component coupling route to alpha,alpha-disubstituted amino acids",

abstract = "We report on a Pd-catalyzed carbonylative α-arylation of azlactones derived from alanine, providing facile access to α,α-disubstituted amino acids after an alcoholysis step. A range of aryl iodides proved to be suitable substrates in this formal four-component approach, providing the desired products in good to high yields. Other amino acids, such as methionine, leucine and phenylalanine could be functionalized in a similar manner with this methodology. The possibility for isotope labeling ( 13C, 2H) was demonstrated, as well as chemoselective transformations of the tricarbonyl-containing molecules.",

keywords = "Amino acids, Azlactones, Carbon monoxide, Catalysis, Palladium",

author = "\{Lobo Just Pinheiro\}, Danielle and Nielsen, \{Dennis Uls{\o}e\} and Giovanni Amarante and Troels Skrydstrup",

year = "2018",

month = aug,

doi = "10.1016/j.jcat.2018.04.027",

language = "English",

volume = "364",

pages = "366–370",

journal = "Journal of Catalysis",

issn = "0021-9517",

publisher = "Academic Press Inc.",

}

Pd-catalyzed carbonylative alpha-arylation of azlactones: A formal four-component coupling route to alpha,alpha-disubstituted amino acids. / Lobo Just Pinheiro, Danielle; Nielsen, Dennis Ulsøe; Amarante, Giovanni et al.
In: Journal of Catalysis, Vol. 364, 08.2018, p. 366–370.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Pd-catalyzed carbonylative alpha-arylation of azlactones: A formal four-component coupling route to alpha,alpha-disubstituted amino acids

AU - Lobo Just Pinheiro, Danielle

AU - Nielsen, Dennis Ulsøe

AU - Amarante, Giovanni

AU - Skrydstrup, Troels

PY - 2018/8

Y1 - 2018/8

N2 - We report on a Pd-catalyzed carbonylative α-arylation of azlactones derived from alanine, providing facile access to α,α-disubstituted amino acids after an alcoholysis step. A range of aryl iodides proved to be suitable substrates in this formal four-component approach, providing the desired products in good to high yields. Other amino acids, such as methionine, leucine and phenylalanine could be functionalized in a similar manner with this methodology. The possibility for isotope labeling ( 13C, 2H) was demonstrated, as well as chemoselective transformations of the tricarbonyl-containing molecules.

AB - We report on a Pd-catalyzed carbonylative α-arylation of azlactones derived from alanine, providing facile access to α,α-disubstituted amino acids after an alcoholysis step. A range of aryl iodides proved to be suitable substrates in this formal four-component approach, providing the desired products in good to high yields. Other amino acids, such as methionine, leucine and phenylalanine could be functionalized in a similar manner with this methodology. The possibility for isotope labeling ( 13C, 2H) was demonstrated, as well as chemoselective transformations of the tricarbonyl-containing molecules.

KW - Amino acids

KW - Azlactones

KW - Carbon monoxide

KW - Catalysis

KW - Palladium

UR - https://www.scopus.com/pages/publications/85048771013

U2 - 10.1016/j.jcat.2018.04.027

DO - 10.1016/j.jcat.2018.04.027

M3 - Journal article

SN - 0021-9517

VL - 364

SP - 366

EP - 370

JO - Journal of Catalysis

JF - Journal of Catalysis

ER -

Pd-catalyzed carbonylative alpha-arylation of azlactones: A formal four-component coupling route to alpha,alpha-disubstituted amino acids

Abstract

Keywords

Access to Document

Library access?

Other files and links

Fingerprint

Cite this