Invertible enantioselectivity in 6'-deoxy-6'-acylamino-beta-isocupreidine-catalyzed asymmetric aza-Morita-Baylis-Hillman reaction: key role of achiral additive. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2009

Invertible enantioselectivity in 6'-deoxy-6'-acylamino-beta-isocupreidine-catalyzed asymmetric aza-Morita-Baylis-Hillman reaction: key role of achiral additive.

Résumé

The beta-ICD (1a) or beta-ICD-amide (1e)-catalyzed aza-Morita-Baylis-Hillman reaction between N-sulfonylimines 3 and alkyl vinyl ketones 4 produced the (R)-enriched adducts 5. By adding a catalytic amount of beta-naphthol (2a), the enantioselectivity of the same reaction was inversed leading to (S)-5 in excellent yields and enantioselectivities. Both aromatic and aliphatic imines are accepted as substrates for this reaction.
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Dates et versions

hal-00428728 , version 1 (29-10-2009)

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Nacim Abermil, Géraldine Masson, Jieping Zhu. Invertible enantioselectivity in 6'-deoxy-6'-acylamino-beta-isocupreidine-catalyzed asymmetric aza-Morita-Baylis-Hillman reaction: key role of achiral additive.. Organic Letters, 2009, 11 (20), pp.4648-51. ⟨10.1021/ol901920s⟩. ⟨hal-00428728⟩
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