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Synlett 1993; 1993(9): 683-685
DOI: 10.1055/s-1993-22571
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Methylaluminum Bis(4-substituted-2,6-di-tert-butylphenoxide) as an Efficient Non-Chelating Lewis Acid

Keiji Maruoka* , Masataka Oishi, Hisashi Yamamoto
  • *School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
19 March 2002 (online)

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The exceptionally bulky methylaluminum bis(4-substituted-2,6-di-tert-butylphenoxide) can be successfully utilized as a highly efficient non-chelating 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 non-chelation controlled diastereoselectivity are present in Grignard and organolithium types of addition to α- and β-alkoxy cyclic ketones.