One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines

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Type
Article
Authors
Mathew, Sam
Sagadevan, Arunachalam
Renn, Dominik cc
Rueping, Magnus cc
KAUST Department
Biological and Environmental Science and Engineering (BESE) Division
Bioscience Program
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
KAUST Grant Number
FCC/1/1974
Date
2021-09-29
Online Publication Date
2021-09-29
Print Publication Date
2021-10-15
Embargo End Date
2022-09-29
Submitted Date
2021-08-02
Permanent link to this record
http://hdl.handle.net/10754/672100

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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%.
Citation
Mathew, S., Sagadevan, A., Renn, D., & Rueping, M. (2021). One-Pot Chemoenzymatic Conversion of Alkynes to Chiral Amines. ACS Catalysis, 12565–12569. doi:10.1021/acscatal.1c03474
Sponsors
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).
Publisher
American Chemical Society (ACS)
Journal
ACS Catalysis
DOI
10.1021/acscatal.1c03474
Additional Links
https://pubs.acs.org/doi/10.1021/acscatal.1c03474
Collections
Articles; Biological and Environmental Science and Engineering (BESE) Division; Bioscience Program; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)