910471-00-0Relevant academic research and scientific papers
Chiral Bronsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines
Itoh, Junji,Fuchibe, Kohei,Akiyama, Takahiko
, p. 4796 - 4798 (2006)
(Chemical Equation Presented) Bronsted, Brassard, Diels, and Alder: Aldimines 1 undergo aza-Diels-Alder reactions with Brassard's diene 2 in the presence of a chiral cyclic phosphate pyridinium salt 4 as a chiral Bronsted acid to give α,β-unsaturated δ-la
Enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines catalyzed by chiral N,N′-dioxide-Yb(OTf)3 complex
Chen, Zhenling,Lin, Lili,Chen, Donghui,Li, Jiangting,Liu, Xiaohua,Feng, Xiaoming
, p. 3088 - 3091 (2010)
The chiral N,N′-dioxide-Yb(OTf)3 complex-catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines has been developed, giving the corresponding α,β-unsaturated δ-lactam derivatives in moderate yields with good enantioselectivities (up to 81% ee and up to 99% ee by single recrystallization) under mild conditions. Isolation of the reaction intermediate indicates that this asymmetric aza-Diels-Alder reaction proceeds through a stepwise Mannich-type pathway.
