Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides

Chemical Communications : Chem Comm
Xia ZhongXiaoming Feng

Abstract

A highly enantioselective [2+2] cycloaddition reaction of alkylidene malonates with the internal C[double bond, length as m-dash]C bond of N-allenamides was developed with a MgII/N,N'-dioxide complex as a catalyst. Various polysubstituted methylenecyclobutanes were afforded in good yields (up to 99%) and excellent enantioselectivities (up to 96% ee) under mild conditions. The utility of the donor-acceptor cyclobutane product was demonstrated as a masked 1,4-dipole in the formal [4+2] annulation reaction with a silyl enol ether.

References

Aug 31, 2002·Chemistry : a European Journal·Léon GhosezJean-François Cordier
Apr 10, 2003·Chemical Reviews·Edward Lee-Ruff, Gabriela Mladenova
Oct 22, 2003·Accounts of Chemical Research·Lin-Li WeiRichard P Hsung
Apr 15, 2004·Angewandte Chemie·Ingo Krossing, Ines Raabe
Sep 29, 2007·Journal of the American Chemical Society·Eda Canales, E J Corey
Jul 8, 2008·Chemistry : a European Journal·Alberto Fernández-TejadaAlberto Avenoza
Mar 16, 2011·Chemistry : a European Journal·Esther GorreaRosa M Ortuño
May 24, 2011·Nature Chemistry·Keiji TaninoMasaaki Miyashita
Jun 28, 2011·Accounts of Chemical Research·XiaoHua LiuXiaoMing Feng
Apr 5, 2013·Chemical Reviews·Ting LuRichard P Hsung
Jul 23, 2013·Angewandte Chemie·Florian de Nanteuil, Jérôme Waser
Oct 2, 2013·Journal of the American Chemical Society·Susannah C Coote, Thorsten Bach
Dec 20, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Francesco SecciPier Paolo Piras
Jun 28, 2014·Chemical Communications : Chem Comm·F de NanteuilJ Waser
Dec 3, 2014·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·Valery M Dembitsky
Jan 7, 2015·Chemical Communications : Chem Comm·Minqiang JiaMarco Bandini
Mar 27, 2015·Angewandte Chemie·Hans-Ulrich Reissig, Reinhold Zimmer
Aug 20, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Alessandro SorrentiRosa M Ortuño
Jan 26, 2016·Accounts of Chemical Research·Jean-Pierre DeprésAndrew E Greene
Jun 9, 2016·Journal of the American Chemical Society·Andreas TrösterThorsten Bach
Jun 22, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Alessandro SorrentiRamon Pons
Oct 3, 2017·Accounts of Chemical Research·Xiaohua LiuXiaoming Feng
Nov 1, 2017·Journal of the American Chemical Society·Kazimer L SkubiTehshik P Yoon

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray

Related Concepts

Related Feeds

Antibodies: Agglutination

Antibody-mediated agglutination is the clumping of cells in the presence of antibody, which binds multiple cells together. This enhances the clearance of pathogens. Find the latest research on antibody-mediated agglutination here.