α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation

Journal of the American Chemical Society
Joel F HooperMichael C Willis

Abstract

Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine.

References

Jul 23, 1996·Proceedings of the National Academy of Sciences of the United States of America·C JamoraA S Lee
Jul 1, 1994·Physical Review. D·D A BauerG Zapalac
Feb 16, 2002·The Journal of Organic Chemistry·Robert V HoffmanFrancisco Cervantes-Lee
Dec 18, 2003·Drug Discovery Today·Hartmuth C Kolb, K Barry Sharpless
Dec 22, 2005·Journal of the American Chemical Society·Michael C Willis, Robert L Woodward
Apr 15, 2006·Science·Ben N G GiepmansRoger Y Tsien
Jun 21, 2006·Bioorganic & Medicinal Chemistry Letters·Aloysius T NchindaEdward D Sturrock
Feb 1, 2007·Journal of the American Chemical Society·Amy H RoyMaurice Brookhart
Oct 10, 2008·Journal of the American Chemical Society·Sohei OmuraIlhyong Ryu
Sep 18, 2009·Chemistry : a European Journal·Scott E Denmark, Thomas Vogler
Oct 6, 2009·Chemical & Pharmaceutical Bulletin·Yasuhiro InuiHiroshi Suemune
Oct 31, 2009·Chemical Reviews·Michael C Willis
Mar 30, 2010·Journal of Medicinal Chemistry·Caterina BissantzMartin Stahl
Jun 11, 2010·American Journal of Therapeutics·Christopher Jamora, Mohamad Iravani
Oct 30, 2010·Journal of the American Chemical Society·Diem H T PhanVy M Dong
Apr 21, 2011·Angewandte Chemie·Carlos González-RodríguezMichael C Willis
Apr 28, 2011·Journal of the American Chemical Society·Xavier BugautFrank Glorius
Jul 12, 2011·Organic Letters·Hui-Jun Zhang, Carsten Bolm
Sep 21, 2011·Angewandte Chemie·Philip LendenMichael C Willis
Nov 9, 2011·Organic Letters·Stephen K MurphyVy M Dong
Feb 14, 2012·Journal of the American Chemical Society·Adrian B ChaplinMichael C Willis
Sep 4, 2012·Journal of the American Chemical Society·Max von DeliusVy M Dong
Jan 18, 2013·Chemistry : a European Journal·Joel F HooperMichael C Willis
Jan 29, 2013·Angewandte Chemie·Michael SchedlerFrank Glorius
Mar 5, 2014·Journal of the American Chemical Society·Qing-An ChenVy M Dong
Mar 13, 2014·Chemistry : a European Journal·Tao ZhangXingwei Li
Dec 20, 2014·Organic & Biomolecular Chemistry·Jiong Yang
Jan 22, 2015·Journal of the American Chemical Society·Qing-An ChenVy M Dong

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Citations

May 20, 2017·Journal of the American Chemical Society·Fei YeTobias Ritter
May 21, 2016·Organic & Biomolecular Chemistry·James D Neuhaus, Michael C Willis
Jul 18, 2017·Journal of the American Chemical Society·Thomas J CoxonMichael C Willis
Apr 16, 2020·Chemistry, an Asian Journal·Tomohiko ShiraiYasunori Yamamoto
Oct 21, 2016·Chemistry : a European Journal·Anaïs BouisseauMichael C Willis
Aug 18, 2017·The Journal of Organic Chemistry·Dachang BaiXingwei Li

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