Microwave acceleration in DABAL-Me 3-mediated amide formation
D Glynn, D Bernier, S Woodward
Index: Glynn, Daniel; Bernier, David; Woodward, Simon Tetrahedron Letters, 2008 , vol. 49, # 39 p. 5687 - 5688
Full Text: HTML
Citation Number: 22
Abstract
Facile direct coupling of esters and secondary amines to afford tertiary amides proceeds under microwave irradiation using the air-stable trimethylaluminium source DABAL-Me3 [(DABCO)(AlMe3) 2]. Excellent yields (88–98%) are attained for cyclic secondary amines in reactions that are complete in 5–16min. The process can be extended to the formation of Weinreb amides (upto 76% from commercial MeNHOMe· HCl) in a one-pot procedure ...
Related Articles:
[Aubert, Catherine; Huard-Perrio, Cecile; Lasne, Marie-Claire Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 19 p. 2837 - 2842]
[Yokoyama, Akihiro; Ohwada, Tomohiko; Shudo, Koichi Journal of Organic Chemistry, 1999 , vol. 64, # 2 p. 611 - 617]
Steps towards a practical synthesis of macrocyclic bisbenzylisoquinolines
[Al-Hiari, Yusuf M.; Bennett, Stephen J.; Cox, Brian; Davies, Robert J.; Khalaf, Abedawn I.; Waigh, Roger D.; Worsley, Alan J. Journal of Heterocyclic Chemistry, 2005 , vol. 42, # 4 p. 647 - 659]
Steps towards a practical synthesis of macrocyclic bisbenzylisoquinolines
[Al-Hiari, Yusuf M.; Bennett, Stephen J.; Cox, Brian; Davies, Robert J.; Khalaf, Abedawn I.; Waigh, Roger D.; Worsley, Alan J. Journal of Heterocyclic Chemistry, 2005 , vol. 42, # 4 p. 647 - 659]
Intra vs intermolecular amidoalkylation of aromatics
[Ishai, D. Ben; Sataty, I.; Peled, N.; Goldshare, R. Tetrahedron, 1987 , vol. 43, # 2 p. 439 - 450]