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Synlett 1995; 1995(7): 719-720
DOI: 10.1055/s-1995-5045
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Evaluation of Aluminum Tris(2,6-di-tert-butyl-4-methylphenoxide) (ATD) as a Lewis Acid Receptor

Keiji Maruoka, Hiroshi Imoto, Hisashi Yamamoto*
  • *School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
31 December 2000 (online)

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Aluminum tris(2,6-di-tert-butyl-4-methylphenoxide) (ATD) has been successfully utilized as a Lewis acid receptor for effective blocking of carbonyl functionality, thereby allowing (1) the conjugate addition of organolithium reagents to α,β-unsaturated ketones, and (2) selective reduction of more hindered ketones. The blocking ability of ATD is evaluated by comparison of the analogous Lewis acid receptors, ATPH and MAD.

conjugate addition - α,β-unsaturated ketones - alkyllithiums - aluminum tris(2,6-di-tert-butyl-4-methylphenoxide) - selective reduction