Enantioselective synthesis of N-C axially chiral compounds by Cu-catalyzed atroposelective aryl amination

Angewandte Chemie
Joanna Wencel-DelordFrançoise Colobert

Abstract

N-C axially chiral compounds have emerged recently as appealing motifs for drug design. However, enantioselective synthesis of such molecules is still poorly developed and surprisingly no metal-catalyzed atroposelective N-arylation have been described. Herein we disclose an unprecedented Cu-catalyzed atroposelective N-C coupling, occurring at room temperature. Such mild reaction conditions, crucial parameter to warrant atropostability of the newly generated products may be reached thank to the use of hypervalent iodines as highly reactive coupling partner. A large panel of the N-C axially chiral compounds is hence afforded in very high enantioselectivities (up to > 99% ee) and good yields (up to 76%). Post-modifications of thus accessed atropisomeric compounds allows further expanding the diversity of these appealing compounds.

References

Jul 24, 1998·Carbohydrate Research·T AreeH Hoier
Mar 18, 2005·Journal of the American Chemical Society·Osamu KitagawaTakeo Taguchi
Aug 24, 2005·Angewandte Chemie·Gerhard BringmannMatthias Breuning
Dec 31, 2008·Angewandte Chemie·Tummanapalli SatyanarayanaHenri B Kagan
Oct 31, 2009·Angewandte Chemie·Eleanor A Merritt, Berit Olofsson
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Nov 5, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Elena SperottoJohannes G de Vries
Dec 9, 2010·Organic Letters·Brent E DialKen D Shimizu
Jun 7, 2011·Bioorganic & Medicinal Chemistry Letters·Shaun R SelnessJoseph B Monahan
Aug 19, 2011·Journal of Medicinal Chemistry·Steven R LaplantePaul J Edwards
Jan 3, 2012·Journal of the American Chemical Society·Seiji ShirakawaKeiji Maruoka
Feb 11, 2012·Journal of the American Chemical Society·Brent E DialKen D Shimizu
Jun 22, 2012·Journal of the American Chemical Society·Shaolin Zhu, David W C MacMillan
Jul 11, 2013·Journal of Medicinal Chemistry·Takashi SuganeShin-ichi Tsukamoto
Oct 1, 2013·Chemical Society Reviews·Jitender Bariwal, Erik Van der Eycken
Apr 18, 2014·Journal of the American Chemical Society·Igors SokolovsEdgars Suna
Jul 16, 2014·Chemical Communications : Chem Comm·Kentaro OkanoTohru Fukuyama
Apr 24, 2015·Chemical Society Reviews·J Wencel-DelordF Colobert
Jun 20, 2015·Journal of the American Chemical Society·Elise CahardMatthew J Gaunt
Aug 19, 2015·Natural Product Reports·Jamie E SmythPaul A Keller
Sep 8, 2015·Journal of the American Chemical Society·Matthew E DienerScott J Miller
Dec 10, 2015·The Journal of Organic Chemistry·Tomoaki HirataOsamu Kitagawa
Feb 11, 2016·Chemical Reviews·Akira Yoshimura, Viktor V Zhdankin
Mar 25, 2017·ACS Medicinal Chemistry Letters·Jianfei WangXiangbo Jia
May 13, 2017·Organic & Biomolecular Chemistry·P Renzi
Jun 24, 2017·Journal of the American Chemical Society·Daniel H Lukamto, Matthew J Gaunt
Dec 11, 2017·Bioorganic & Medicinal Chemistry Letters·Peter W Glunz
Jan 31, 2018·Future Medicinal Chemistry·Sean T Toenjes, Jeffrey L Gustafson
Feb 9, 2018·Accounts of Chemical Research·Yong-Bin Wang, Bin Tan
Jun 30, 2018·Angewandte Chemie·Nibadita PurkaitBerit Olofsson
Jul 18, 2018·Journal of Medicinal Chemistry·Jayaraman ChandrasekharStephane Perreault
Jan 24, 2019·Organic & Biomolecular Chemistry·Takashi MinoMasami Sakamoto

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Citations

Jun 20, 2020·Chemistry : a European Journal·Alessandro CastrogiovanniChristof Sparr
Oct 20, 2020·Chemistry : a European Journal·Vinzenz Thönnißen, Frederic W Patureau
Mar 30, 2021·Chemical Reviews·Jun Kee ChengBin Tan
Apr 27, 2021·Angewandte Chemie·Matteo LanziJoanna Wencel-Delord

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