One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

Sam Mathew; Arunachalam Sagadevan; Dominik Renn; Magnus Rueping

doi:10.1021/acscatal.1c03474

One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

Sam Mathew, Arunachalam Sagadevan, Dominik Renn, Magnus Rueping

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, with ee > 99%.

Original language	English (US)
Pages (from-to)	12565-12569
Number of pages	5
Journal	ACS Catalysis
DOIs	https://doi.org/10.1021/acscatal.1c03474
State	Published - Sep 29 2021

ASJC Scopus subject areas

Catalysis

Access to Document

10.1021/acscatal.1c03474

Cite this

@article{1d86b393dd85458ab9fc4ee24dcb36bd,

title = "One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines",

abstract = "A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, with ee > 99%.",

author = "Sam Mathew and Arunachalam Sagadevan and Dominik Renn and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2021-10-05 Acknowledged KAUST grant number(s): FCC/1/1974 Acknowledgements: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (FCC/1/1974).",

year = "2021",

month = sep,

day = "29",

doi = "10.1021/acscatal.1c03474",

language = "English (US)",

pages = "12565--12569",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

AU - Mathew, Sam

AU - Sagadevan, Arunachalam

AU - Renn, Dominik

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2021-10-05 Acknowledged KAUST grant number(s): FCC/1/1974 Acknowledgements: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (FCC/1/1974).

PY - 2021/9/29

Y1 - 2021/9/29

N2 - A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, with ee > 99%.

AB - A one-pot chemoenzymatic sequential cascade for the synthesis of chiral amines from alkynes was developed. In this integrated approach, just ppm amounts of gold catalysts enabled the conversion of alkynes to ketones (>99%) after which a transaminase was used to catalyze the production of biologically valuable chiral amines in a good yield (up to 99%) and enantiomeric excess (>99%). A preparative scale synthesis of (S)-methylbenzylamine and (S)-4-methoxy-methylbenzylamine from its alkyne form gave a yield of 59 and 92%, respectively, with ee > 99%.

UR - http://hdl.handle.net/10754/672100

UR - https://pubs.acs.org/doi/10.1021/acscatal.1c03474

U2 - 10.1021/acscatal.1c03474

DO - 10.1021/acscatal.1c03474

M3 - Article

SN - 2155-5435

SP - 12565

EP - 12569

JO - ACS Catalysis

JF - ACS Catalysis

ER -

One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this