Conjugate Addition of Reactive Carbanions to α,β-Unsaturated Ketones in the Presence of ATPH

Keiji Maruoka; Itsuro Shimada; Hiroshi Imoto; Hisashi Yamamoto

doi:10.1055/s-1994-22912

Synlett 1994; 1994(7): 519-520
DOI: 10.1055/s-1994-22912

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Conjugate Addition of Reactive Carbanions to α,β-Unsaturated Ketones in the Presence of ATPH

Keiji Maruoka^* , Itsuro Shimada, Hiroshi Imoto, Hisashi Yamamoto

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

Abstract

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Aluminum tris(2,6-diphenylphenoxide) (ATPH) has been successfully utilized for effective blocking of carbonyl moieties, thereby allowing the conjugate addition of organolithium reagents to α,β-unsaturated ketones. In particular, conjugate addition of lithium alkynides and thermally unstable lithium carbenoids, which are very difficult to achieve in organocopper chemistry, are realized with α,β-unsaturated ketone/ATPH complexes.

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