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

Chemical Science
Lu ZhangLei Liu

Abstract

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.

References

Nov 3, 1975·Biochemical and Biophysical Research Communications·N Relyea, R R Rando
Aug 14, 2003·Chemical Reviews·Keiji Maruoka, Takashi Ooi
Aug 16, 2003·Science·Jason W ChinPeter G Schultz
Nov 4, 2004·Trends in Genetics : TIG·T Ashton Cropp, Peter G Schultz
Dec 16, 2004·Angewandte Chemie·Lei Wang, Peter G Schultz
Jun 9, 2005·Angewandte Chemie·Edwin Vedejs, Mara Jure
Aug 3, 2005·Proceedings of the National Academy of Sciences of the United States of America·Jian-Xin JiAlbert S C Chan
Feb 16, 2006·Journal of the American Chemical Society·Colin J DunsmoreNicholas J Turner
Apr 19, 2007·Chemistry, an Asian Journal·Yusuke ShimadaYoshiaki Nishibayashi
Jun 21, 2007·Chemical Communications : Chem Comm·Gareth R A Adair, Jonathan M J Williams
Aug 10, 2007·Journal of the American Chemical Society·Daniel H Ess, K N Houk
Nov 7, 2007·Chemical Reviews·Takahiko Akiyama
Jun 12, 2008·Journal of the American Chemical Society·Luis Simón, Jonathan M Goodman
Jul 11, 2008·Journal of the American Chemical Society·Daniel H Ess, K N Houk
Sep 30, 2008·Journal of the American Chemical Society·Constance V VossWolfgang Kroutil
Jan 2, 2010·Current Opinion in Chemical Biology·Nicholas J Turner
May 22, 2010·Organic & Biomolecular Chemistry·Willem-Jan van Zeist, F Matthias Bickelhaupt
Oct 29, 2011·Angewandte Chemie·Alison E WendlandtShannon S Stahl
Jan 28, 2012·Chemical Society Reviews·Chao Zheng, Shu-Li You
Feb 24, 2012·Chemical Society Reviews·Zhuangzhi ShiNing Jiao
Mar 17, 2012·Nature·Ilija Čorić, Benjamin List
Jul 3, 2013·Journal of the American Chemical Society·Diego GhislieriNicholas J Turner
Sep 13, 2013·Journal of the American Chemical Society·Aaron D LacknerF Dean Toste
Sep 26, 2013·Chemical Society Reviews·Michał RachwalskiFloris P J T Rutjes
Jan 23, 2015·Accounts of Chemical Research·Chen ZhuTakahiko Akiyama
Jun 11, 2015·Chemical Reviews·Dong Wang, Didier Astruc

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Citations

Dec 3, 2021·Organic & Biomolecular Chemistry·Fan-Jie MengLei Shi

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