Self-condensation of N-tert-butanesulfinyl aldimines: application to the rapid asymmetric synthesis of biologically important amine-containing compounds

Organic Letters
Laurie B Schenkel, Jonathan A Ellman

Abstract

[reaction: see text] Highly diastereoselective intra- and intermolecular self-condensation reactions of N-tert-butanesulfinyl aldimines have been developed and applied to the rapid, asymmetric synthesis of trans-2-aminocyclopentanecarboxylic acid and the drug candidate SC-53116. Key to both syntheses is a novel microwave-assisted reaction in which N-sulfinyl aldimines are cleanly converted into nitriles in high-yielding concerted elimination processes.

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Citations

May 8, 2009·Chemical Society Reviews·Franck FerreiraAlejandro Pérez-Luna
Jul 1, 2017·The Journal of Organic Chemistry·Alejandro LahosaMiguel Yus
Aug 27, 2014·Natural Product Reports·Jeremy Robertson, Kiri Stevens
May 12, 2012·Organic & Biomolecular Chemistry·Ramakrishna Edupuganti, Franklin A Davis
Feb 15, 2011·Chemistry : a European Journal·Xiao-Feng XiongYing-Chun Chen
May 14, 2010·The Journal of Organic Chemistry·Franklin A Davis, Naresh Theddu
Sep 5, 2008·Journal of the American Chemical Society·Lone Nielsen, Troels Skrydstrup
Oct 18, 2008·The Journal of Organic Chemistry·Paul E ZhichkinW Martin Rennells
Jul 14, 2006·Chemical Reviews·Vittorio FarinaJinhua J Song
Apr 28, 2010·Chemical Reviews·MaryAnn T RobakJonathan A Ellman
Jun 15, 2012·The Journal of Organic Chemistry·Juan F ColladosMiguel Yus
Mar 9, 2011·The Journal of Organic Chemistry·Filip ColpaertNorbert De Kimpe
Mar 22, 2014·Organic Letters·Hannah E BartrumJean-François Poisson
Mar 5, 2014·The Journal of Organic Chemistry·Martin HennumOdile Eisenstein
May 8, 2019·The Journal of Organic Chemistry·Alejandro LahosaFrancisco Foubelo
Apr 14, 2005·Journal of the American Chemical Society·Amelia A FullerAnna K Mapp
Aug 27, 2005·The Journal of Organic Chemistry·Hillary M Peltier, Jonathan A Ellman
Sep 15, 2005·Journal of the American Chemical Society·José Luis García RuanoAlejandro Parra

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