Dynamic kinetic resolution of bis-aryl succinic anhydrides: enantioselective synthesis of densely functionalised γ-butyrolactones

作者: Romain Claveau , Brendan Twamley , Stephen J. Connon

DOI: 10.1039/C8CC00609A

关键词:

摘要: The efficient Dynamic Kinetic Resolution (DKR) of disubstituted anhydrides has been shown to be possible for the first time. Using an ad hoc designed organocatalyst and enantio- diastereoselective cycloaddition process with aldehydes, stereochemically complex γ-butyrolactone derivatives can obtained - control over three contiguous stereocentres, one which is all carbon quaternary.

参考文章(49)
Fernando F. Huerta, Alexander B. E. Minidis, Jan-E. Bäckvall, Racemisation in asymmetric synthesis. Dynamic kinetic resolution and related processes in enzyme and metal catalysis Chemical Society Reviews. ,vol. 30, pp. 321- 331 ,(2001) , 10.1039/B105464N
S. Caddick, K. Jenkins, Dynamic resolutions in asymmetric synthesis Chemical Society Reviews. ,vol. 25, pp. 447- 456 ,(1996) , 10.1039/CS9962500447
Aldo Peschiulli, Barbara Procuranti, Cornelius J. O' Connor, Stephen J. Connon, Synergistic organocatalysis in the kinetic resolution of secondary thiols with concomitant desymmetrization of an anhydride Nature Chemistry. ,vol. 2, pp. 380- 384 ,(2010) , 10.1038/NCHEM.584
Ryoji Noyori, Makoto Tokunaga, Masato Kitamura, Stereoselective Organic Synthesis via Dynamic Kinetic Resolution Bulletin of the Chemical Society of Japan. ,vol. 68, pp. 36- 55 ,(1995) , 10.1246/BCSJ.68.36
John M. Keith, Jay F. Larrow, Eric N. Jacobsen, Practical Considerations in Kinetic Resolution Reactions Advanced Synthesis & Catalysis. ,vol. 343, pp. 5- 26 ,(2001) , 10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO;2-I
Francesco Manoni, Claudio Cornaggia, James Murray, Sean Tallon, Stephen J. Connon, Catalytic, enantio- and diastereoselective synthesis of γ-butyrolactones incorporating quaternary stereocentres Chemical Communications. ,vol. 48, pp. 6502- 6504 ,(2012) , 10.1039/C2CC32147E
Eric A. Bercot, Tomislav Rovis, A mild and efficient catalytic alkylative monofunctionalization of cyclic anhydrides. Journal of the American Chemical Society. ,vol. 124, pp. 174- 175 ,(2002) , 10.1021/JA017086W
Michael Seitz, Oliver Reiser, Synthetic approaches towards structurally diverse γ-butyrolactone natural-product-like compounds Current Opinion in Chemical Biology. ,vol. 9, pp. 285- 292 ,(2005) , 10.1016/J.CBPA.2005.03.005
A. Verley, Fr. Bölsing, Ueber quantitative Esterbildung und Bestimmung von Alkoholen resp. Phenolen Berichte der deutschen chemischen Gesellschaft. ,vol. 34, pp. 3354- 3358 ,(1901) , 10.1002/CBER.19010340318
Alan C. Spivey, Paul McDaid, Asymmetric Acyl Transfer Reactions ChemInform. ,vol. 40, pp. 287- 329 ,(2007) , 10.1002/9783527610945.CH8