A direct and mild conversion of tertiary aryl amides to methyl esters using trimethyloxonium tetrafluoroborate: A very useful complement to directed metalation …
GE Keck, MD McLaws, TT Wager
Index: Keck, Gary E; McLaws, Mark D; Wager, Travis T Tetrahedron, 2000 , vol. 56, # 51 p. 9875 - 9883
Full Text: HTML
Citation Number: 42
Abstract
The scope and generality of a direct process for the conversion of tertiary amides directly to methyl esters has been investigated. The process involves a two-step, one pot procedure in which a tertiary amide is first treated with trimethyloxonium tetrafluoroborate to generate an imidate intermediate which is then hydrolyzed, generally by the addition of saturated aqueous sodium bicarbonate solution. Although this process fails for aliphatic amides, ...
Related Articles:
Total synthesis of acerogenins E, G and K, and centrolobol
[Ogura, Tetsuhiro; Usuki, Toyonobu Tetrahedron, 2013 , vol. 69, # 13 p. 2807 - 2815]
[Wang, Azhong; Jiang, Huanfeng Journal of the American Chemical Society, 2008 , vol. 130, # 15 p. 5030 - 5031]
[Kaganovsky, Luba; Gelman, Dmitri; Rueck-Braun, Karola Journal of Organometallic Chemistry, 2010 , vol. 695, # 2 p. 260 - 266]
[Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2012 , vol. 68, # 24 p. 4701 - 4709]
[Li, Pan; Zhao, Jingjing; Lang, Rui; Xia, Chungu; Li, Fuwei Tetrahedron Letters, 2014 , vol. 55, # 2 p. 390 - 393]