Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes†
نویسندگان
چکیده
A metal-free stereoselective reductive coupling reaction between isatins and aldehydes is reported. The reaction relies on commercial diethyl phosphite (∼€70 kg-1) as the stoichiometric reductant. Base-catalyzed Pudovik addition and phosphonate/phosphate rearrangement achieved polarity inversion on the isatin, and the derived carbanions were trapped by aldehydes with subsequent dialkoxyphosphinyl migration. Chiral iminophosphoranes were used as basic catalysts to achieve high diastereo- and enantioselectivities with excellent yields.
منابع مشابه
Diastereo- and Enantioselective Reactions of Bis(pinacolato)diboron, 1,3-Enynes, and Aldehydes Catalyzed by an Easily Accessible Bisphosphine–Cu Complex
Catalytic enantioselective multicomponent processes involving bis(pinacolato)diboron [B2(pin)2], 1,3-enynes, and aldehydes are disclosed; the resulting compounds contain a primary C-B(pin) bond, as well as alkyne- and hydroxyl-substituted tertiary carbon stereogenic centers. A critical feature is the initial enantioselective Cu-B(pin) addition to an alkyne-substituted terminal alkene. This and ...
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