Stereoselective alkylation of alpha,beta-unsaturated imines via C-H bond activation.

Journal of the American Chemical Society
Denise A ColbyJonathan A Ellman

Abstract

The stereoselective alkylation of alpha,beta-unsaturated imines via C-H activation followed by imine hydrolysis produces tri- and tetrasubstituted alpha,beta-unsaturated aldehydes. In the presence of a rhodium catalyst, alpha,beta-unsaturated N-benzyl imines derived from methacrolein, crotonaldehyde, and tiglic aldehyde undergo directed C-H activation at the beta-position and react with terminal alkenes and alkynes to form the tri- and tetrasubstituted alpha,beta-unsaturated imines with very high stereoselectivity. Hydrolysis to provide alpha,beta-unsaturated aldehydes can be performed under carefully controlled conditions that maintain the stereochemistry of the beta-alkylated imine products. Alternatively, for beta-alkylation products of the N-benzyl imine of methacrolein, hydrolysis can be performed under conditions that provide complete isomerization to the E isomer.

References

Aug 9, 2003·Journal of the American Chemical Society·Eric M Ferreira, Brian M Stoltz
Jun 10, 2004·Journal of the American Chemical Society·Reema K ThaljiRobert G Bergman
Aug 13, 2005·The Journal of Organic Chemistry·Reema K ThaljiJonathan A Ellman

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Citations

Dec 14, 2011·Accounts of Chemical Research·Denise A ColbyJonathan A Ellman
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Feb 28, 2008·Journal of the American Chemical Society·Denise A ColbyJonathan A Ellman
Sep 6, 2011·Chemical Communications : Chem Comm·Yoichiro KuninobuKazuhiko Takai
Aug 2, 2008·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Akio Saito
Jun 25, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Giovanna Bosica, Roderick Abdilla
Jan 27, 2017·Chemical Reviews·Zhe DongGuangbin Dong
Apr 8, 2017·Journal of the American Chemical Society·Yan XuGuangbin Dong
Oct 28, 2016·Chemistry : a European Journal·Takanori ShibataKyalo Stephen Kanyiva
Oct 31, 2012·Angewandte Chemie·James W Walton, Jonathan M J Williams
Dec 6, 2014·Angewandte Chemie·Stefan A RuiderErick M Carreira
Aug 27, 2010·Chemistry : a European Journal·Tetsuya Satoh, Masahiro Miura
Jun 22, 2012·Organic & Biomolecular Chemistry·Adam D J Calow, Andrew Whiting
Jul 6, 2020·Chirality·Tsung-Che ChangKatsunori Tanaka
Jun 28, 2012·Chemistry : a European Journal·David Y-K Chen, So Won Youn
Dec 14, 2011·Chemistry : a European Journal·Thibaut Courant, Géraldine Masson
Mar 11, 2011·Chemical Society Reviews·Lindsay McMurrayMatthew J Gaunt
Aug 8, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Abdollah NeshatJoseph A R Schmidt
May 15, 2009·Chemistry : a European Journal·Praew Thansandote, Mark Lautens
Aug 14, 2013·Angewandte Chemie·Kazuhiro OkamotoKouichi Ohe
Jan 24, 2012·Organic & Biomolecular Chemistry·Jared W RigoliJennifer M Schomaker

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