Enantioselective organocatalytic alkylation of aldehydes and enals driven by the direct photoexcitation of enamines

Journal of the American Chemical Society
Mattia SilviPaolo Melchiorre

Abstract

Disclosed herein is a photo-organocatalytic enantioselective α- and γ-alkylation of aldehydes and enals, respectively, with bromomalonates. The chemistry uses a commercially available aminocatalyst and occurs under illumination by a fluorescent light bulb in the absence of any external photoredox catalyst. Mechanistic investigations reveal the previously hidden ability of transiently generated enamines to directly reach an electronically excited state upon light absorption while successively triggering the formation of reactive radical species from the organic halides. At the same time, the ground state chiral enamines provide effective stereochemical induction for the enantioselective alkylation process.

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Citations

Apr 23, 2015·Journal of the American Chemical Society·Łukasz WoźniakPaolo Melchiorre
Apr 14, 2016·Chemical Reviews·Davide RavelliMaurizio Fagnoni
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Jun 9, 2016·Journal of the American Chemical Society·Ana Bahamonde, Paolo Melchiorre
Jul 22, 2016·Organic Letters·Shu-Wei Wu, Feng Liu
Sep 1, 2016·Journal of the American Chemical Society·Xiaoqiang HuangEric Meggers
Sep 16, 2016·Journal of the American Chemical Society·Ming YanPhil S Baran
Dec 22, 2016·Journal of the American Chemical Society·Wei DingWen-Jing Xiao
Apr 13, 2017·Journal of the American Chemical Society·Mattia SilviVarinder K Aggarwal
Apr 19, 2016·Angewandte Chemie·Mark L SpellJustin R Ragains
Dec 17, 2015·Chemical Science·Megan A Cismesia, Tehshik P Yoon
Apr 30, 2017·Chemistry : a European Journal·Igor D Jurberg
Apr 1, 2016·Chemical Communications : Chem Comm·Ran DingTeck-Peng Loh
Nov 3, 2016·Chemical Society Reviews·Vanesa Marcos, José Alemán
Nov 21, 2015·Nature Chemistry·Thomas BrojaKirsten Zeitler
Jun 12, 2018·Organic & Biomolecular Chemistry·Ioanna K SideriChristoforos G Kokotos
Jun 28, 2018·Organic & Biomolecular Chemistry·Abdul MotalebPradip Maity
Feb 20, 2018·Angewandte Chemie·Leyre MarzoBurkhard König
Sep 14, 2018·Organic & Biomolecular Chemistry·Venkata M D PadmajaChandrakumar Appayee
Sep 27, 2018·Organic & Biomolecular Chemistry·Haruna MatsuiTomoko Yajima
Nov 14, 2018·Chemical Communications : Chem Comm·Qiong YangShaolin Zhou
Oct 20, 2018·Angewandte Chemie·Luca BuzzettiPaolo Melchiorre
Feb 2, 2018·Nature·Mattia Silvi, Paolo Melchiorre
Sep 20, 2019·Organic & Biomolecular Chemistry·Chunhui JiangHongfei Lu
Sep 11, 2019·Beilstein Journal of Organic Chemistry·Barbara Reiß, Hans-Achim Wagenknecht

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