Abstract
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 reagents exhibits high diastereoselectivity not observable with ordinary Lewis acids. Furthermore, high levels of nonchelation controlled diastereoselectivity are present in Grignard- and organolithium-types of addition to α- and β-alkoxy cyclic ketones in the presence of MAD or MABR.
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