Issue 17, 2020

Redox deracemization of β,γ-alkynyl α-amino esters


The first non-enzymatic redox deracemization method using molecular oxygen as the terminal oxidant has been described. The one-pot deracemization of β,γ-alkynyl α-amino esters consisted of a copper-catalyzed aerobic oxidation and chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation with excellent functional group compatibility. By using benzothiazoline as the reducing reagent, an exclusive chemoselectivity at the C[double bond, length as m-dash]N bond over the C[triple bond, length as m-dash]C bond was achieved, allowing for efficient deracemization of a series of α-amino esters bearing diverse α-alkynyl substituent patterns. The origins of chemo- and enantio-selectivities were elucidated by experimental and computational mechanistic investigation. The generality of the strategy is further demonstrated by efficient deracemization of β,γ-alkenyl α-amino esters.

Graphical abstract: Redox deracemization of β,γ-alkynyl α-amino esters

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Article information

Article type
Edge Article
17 Feb 2020
07 Apr 2020
First published
21 Apr 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 4444-4449

Redox deracemization of β,γ-alkynyl α-amino esters

L. Zhang, R. Zhu, A. Feng, C. Zhao, L. Chen, G. Feng and L. Liu, Chem. Sci., 2020, 11, 4444 DOI: 10.1039/D0SC00944J

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