Enantioselective copper-catalyzed reductive coupling of alkenylazaarenes with ketones.

Journal of the American Chemical Society
Aakarsh SaxenaHon Wai Lam

Abstract

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of C═N-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection.

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Citations

Oct 12, 2012·Journal of the American Chemical Society·Daniel BestHon Wai Lam
Oct 11, 2013·Journal of the American Chemical Society·Shaolin ZhuStephen L Buchwald
Dec 18, 2013·The Journal of Organic Chemistry·Daniel Best, Hon Wai Lam
May 11, 2013·Organic Letters·Alain J Simpson, Hon Wai Lam
Mar 5, 2016·Journal of the American Chemical Society·Joseba IzquierdoClaudio Palomo
Apr 29, 2016·Journal of the American Chemical Society·Jeffrey S BandarStephen L Buchwald
Jun 28, 2016·Journal of the American Chemical Society·Stig D FriisStephen L Buchwald
Jul 28, 2016·Chemical Reviews·Abraham J JordanJoseph P Sadighi
Mar 21, 2017·Journal of the American Chemical Society·Xiao-Feng WeiMotomu Kanai
Dec 20, 2014·Chemical Communications : Chem Comm·Guoying ZhangHanmin Huang
Feb 18, 2016·Chemical Communications : Chem Comm·Joshua J SmithHon Wai Lam
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Oct 2, 2012·Angewandte Chemie·Alan R BurnsHon Wai Lam
Sep 15, 2018·Chemical Communications : Chem Comm·Xiao XuFeng Liu
Jun 13, 2019·Chemical Communications : Chem Comm·Baokun QiaoZhiyong Jiang
Jan 10, 2020·Chemistry : a European Journal·Timothy James Donohoe, Hamish Hepburn
Dec 4, 2019·Chemistry : a European Journal·Jung Tae HanJaesook Yun
Jul 26, 2012·Chemistry : a European Journal·Charlene Fallan, Hon Wai Lam
Jan 16, 2020·Chemical Communications : Chem Comm·Ya-Li ZengQuan-Zhong Liu
Nov 24, 2020·Angewandte Chemie·Won Jun JangJaesook Yun
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Jan 27, 2019·Organic Letters·Xu-Cheng Gan, Liang Yin
Dec 2, 2020·Journal of the American Chemical Society·Pengfei HuPhil S Baran
May 14, 2020·Accounts of Chemical Research·Richard Y Liu, Stephen L Buchwald

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