Gold(I)-Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Alkynes: Access to Original Heterospirocycles

Organic Letters
Kossi Efouako SoklouKaren Plé

Abstract

We report here a simple and robust gold-catalyzed annulation reaction, giving N- and O-spirocycles in good to excellent yields. We have prepared a library of protected amines and tertiary alcohols that give, upon cyclization with alkynes, a representative set of heterospirocycles and illustrate reaction compatibility with diverse functional groups. A change in catalytic activity is possible by modifying the solvent, and two original tricyclic spirocycles were synthesized in a tandem reaction.

References

Jul 11, 2008·Chemical Reviews·Zigang LiChuan He
Nov 26, 2009·Chemistry : a European Journal·Jan P WeyrauchJan W Bats
Mar 2, 2010·The Journal of Organic Chemistry·Masahiro EgiShuji Akai
Jun 5, 2010·Journal of the American Chemical Society·Longwu YeLiming Zhang
Apr 1, 2011·Chemical Communications : Chem Comm·Matthias Rudolph, A Stephen K Hashmi
Apr 14, 2011·Organic & Biomolecular Chemistry·Benito AlcaideJosé Miguel Alonso
Jun 8, 2011·Beilstein Journal of Organic Chemistry·F Dean Toste
Jun 8, 2011·Beilstein Journal of Organic Chemistry·Benito Alcaide, Pedro Almendros
Jun 14, 2013·The Journal of Organic Chemistry·Sarvesh KumarConrad Santini
Nov 10, 2013·Beilstein Journal of Organic Chemistry·F Dean Toste
Jan 17, 2014·Accounts of Chemical Research·Benito Alcaide, Pedro Almendros
Mar 19, 2014·Accounts of Chemical Research·Cynthia M Friend, A Stephen K Hashmi
Apr 10, 2014·Chemical Reviews·Vladimir A D'yakonovUsein M Dzhemilev
Jul 9, 2014·Chemical Reviews·Erick M Carreira, Thomas C Fessard
Dec 9, 2014·Journal of the American Chemical Society·Woon-Yew Siau, Jeffrey W Bode
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren
May 11, 2016·ACS Combinatorial Science·Silvia StotaniFabrizio Giordanetto
Nov 20, 2016·Chemistry : a European Journal·Gerhard MüllerJürgen Bajorath
Jan 18, 2018·Chemistry : a European Journal·Alexander A KirichokPavel K Mykhailiuk
Jan 26, 2018·Bioorganic & Medicinal Chemistry·Gemma C GearyChristopher J Moody
Jun 29, 2018·Chemical Society Reviews·Aishun DingRamon Rios

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