Distinct chemoselectivity in the reaction of N-(thio)phosphoryl imines with diethylzinc

Ein kooperativer Katalysator aus einer weichen Lewis‐Säure und einer „harten“ Brønsted‐Base katalysierte die Titelreaktion. Die N‐Thiophosphinoyl‐Gruppe der Ketimine war entscheidend zur Überwindung der hohen Aktivierungsbarriere durch die „Weich‐weich“‐Wechselwirkung von Schwefel und Kupfer. Mannich‐Addukte mit einem tetrasubstituierten Stereozentrum wurden mit ausgezeichneten Diastereo‐ und Enantioselektivitäten hergestellt. TANIAPHOS=Ferrocenyl‐Ligand.

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Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines

Yin

Takada

Kumagai

et al. 2013

Angewandte Chemie

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Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines

et al. 2013

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Distinct Chemoselectivity in the Reaction of N‐(Thio)phosphoryl Imines with Diethylzinc.

Wang

et al. 2007

ChemInform

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Organo-phosphorus compounds S 0080Distinct Chemoselectivity in the Reaction of N-(Thio)phosphoryl Imines with Diethylzinc. -Reaction of N-(thio)phosphoryl imines (I) with diethylzinc in toluene proceeds with unexpected chemoselectivity to afford the reduction products (II) exclusively. In contrast, in the presence of strongly coordinating TMEDA the reaction proceeds with formation of the ethyl adduct [cf. (V)] in high yields. Mixtures of both reduction and ethylation products are formed in more polar solvents in the absence of other additives. The reaction mechanism is discussed and a coordinative interaction between imine, solvent, diethylzinc and additive is proposed. -(MA, X.; XU, X.; WANG, C.; ZHAO*, G.; ZHOU, Z.; TANG, C.; J.

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Distinct chemoselectivity in the reaction of N-(thio)phosphoryl imines with diethylzinc

Cited by 9 publications

References 25 publications

Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines

Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines

Direct Catalytic Asymmetric Vinylogous Mannich‐Type Reaction of γ‐Butenolides with Ketimines

Distinct Chemoselectivity in the Reaction of N‐(Thio)phosphoryl Imines with Diethylzinc.

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