Methylaluminum bis(4-substituted-2,6-di-tert-butylphenoxide) as an efficient nonchelating Lewis acid: Application to asymmetric Diels-Alder reaction and diastereoselective alkylation to alkoxy carbonyl substrates
作者:Keiji Maruoka、Masataka Oishi、Kei Shiohara、Hisashi Yamamoto
DOI:10.1016/s0040-4020(01)85366-7
日期:1994.1
The exceptionally bulky methylaluminum bis(4-substituted-2,6-di-tert-butylphenoxide) such as MAD or MABR can be successfully utilized as a highly efficient nonchelating Lewis acid for achieving high stereoselectivity in 1,n asymmetric induction in cyclic as well as acyclic systems. Thus, Diels-Alder reaction of the acrylate of D-pantolactone and cyclopentadiene in the presence of such bulky organoaluminum
异常庞大的甲基铝双(4-取代-2,6-二叔丁基苯氧化物),例如MAD或MABR,可以成功地用作高效的非螯合路易斯酸,从而在环状1,n不对称诱导中实现高立体选择性作为非循环系统。因此,在这种庞大的有机铝试剂的存在下,D-泛内酯的丙烯酸酯与环戊二烯的丙烯酸酯的狄尔斯-阿尔德反应表现出高的非对映选择性,这是普通路易斯酸所不能观察到的。此外,在存在MAD或MABR的情况下,除α-和β-烷氧基环状酮外,格氏和有机锂类型的非螯合控制的非对映选择性水平较高。