Aluminum Tris(2,6-diphenylphenoxide) (ATPH) as an Extremely Selective Activator of Less Hindered Aldehyde Carbonyls

Keiji Maruoka; Susumu Saito; Hisashi Yamamoto

doi:10.1055/s-1994-22881

Synlett 1994; 1994(6): 439-440
DOI: 10.1055/s-1994-22881

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Aluminum Tris(2,6-diphenylphenoxide) (ATPH) as an Extremely Selective Activator of Less Hindered Aldehyde Carbonyls

Keiji Maruoka^* , Susumu Saito, Hisashi Yamamoto

^*School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan

Abstract

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The bulky, oxygenophilic aluminum tris(2,6-diphenylphenoxide) (ATPH) is introduced for use in the precise recognition and activation of structurally or electronically similar aldehydes by selective Lewis acid-base complex formation. The exceedingly high recognition and activation ability of ATPH for aldehyde functionalities is striking in comparison with other bulky Lewis acids such as MAD and MAPH. This chemistry has been applied to chemoselective hetero-Diels-Alder and aldol reactions of two different sterically less hindered aldehydes.

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