用于与α-酰氧基丙烯醛进行对映选择性狄尔斯-阿尔德反应的手性1,1'-联萘-2,2'-二铵盐催化剂。
Chiral 1,1'-binaphthyl-2,2'-diammonium salt catalysts for the enantioselective Diels-Alder reaction with alpha-acyloxyacroleins.
作者信息
Sakakura Akira, Suzuki Kenji, Nakano Kazuhiko, Ishihara Kazuaki
机构信息
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Japan.
出版信息
Org Lett. 2006 May 25;8(11):2229-32. doi: 10.1021/ol060490l.
[reaction: see text] A diammonium salt of chiral 1,1'-binaphthyl-2,2'-diamine and trifluoromethanesulfonimide (Tf(2)NH) shows excellent catalytic activity and enantioselectivity for the Diels-Alder reaction of alpha-acyloxyacroleins with cyclic dienes. For example, in the presence of 5 mol % of the ammonium catalyst, the Diels-Alder reaction of alpha-(cyclohexanecarbonyloxy)acrolein with cyclopentadiene proceeded in EtCN at -75 degrees C to give the adducts in 88% yield with 92% exo and 91% ee. This catalyst can be easily prepared in situ by mixing the commercially available chiral diamine and Tf(2)NH.
[反应：见正文] 手性1,1'-联萘-2,2'-二胺的二铵盐与三氟甲磺酸亚胺（Tf(2)NH）对α-酰氧基丙烯醛与环状二烯的狄尔斯-阿尔德反应显示出优异的催化活性和对映选择性。例如，在5 mol%的铵催化剂存在下，α-(环己烷羰基氧基)丙烯醛与环戊二烯的狄尔斯-阿尔德反应在乙腈中于-75℃进行，以88%的产率得到加合物，外型异构体比例为92%，对映体过量值为91%。该催化剂可通过将市售手性二胺与Tf(2)NH混合轻松原位制备。
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