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Article Dans Une Revue ACS Catalysis Année : 2022

Enantioselective Au(I)-Catalyzed Multicomponent Annulations via Tethered Counterion-Directed Catalysis

Résumé

Gold(I) complexes of a new chiral phosphoric acid functionalized phosphine of the CPA-Phos series enable the enantioselective multicomponent reactions between aldehydes, hydroxylamines and cyclic yne-enones, leading to 3,4-dihydro-1H-furo[3,4-d][1,2]oxazines. This represents the first example of highly enantioselective multicomponent reaction in gold(I) catalysis. The reactions proceed at low catalyst loading, provide high yields, total diastereoselectivity and enantiomeric excesses up to 99%. Silver-free conditions can be applied. The method has a very broad scope, as it applies to both aliphatic and aromatic aldehydes and hydroxylamines, to a variety of cyclic yne-enones, as well as to yne-enone derived oximes. DFT calculations are reported that enlighten the enantiocontrol pathway.
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Dates et versions

hal-03769461 , version 1 (05-09-2022)

Identifiants

Citer

Zhenhao Zhang, Nazarii Sabat, Gilles Frison, Angela Marinetti, Xavier Guinchard. Enantioselective Au(I)-Catalyzed Multicomponent Annulations via Tethered Counterion-Directed Catalysis. ACS Catalysis, 2022, 12 (7), pp.4046-4053. ⟨10.1021/acscatal.2c00120⟩. ⟨hal-03769461⟩
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