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Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes |
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| Authors: | Matthew A Horwitz Naoya Tanaka Takuya Yokosaka Daisuke Uraguchi Jeffrey S Johnson Takashi Ooi |
| Institution: | a Department of Chemistry , The University of North Carolina at Chapel Hill , Chapel Hill , NC 27599 , USA . Email: ;b Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry , Graduate School of Engineering , Nagoya University , Furo-cho D2-1, Chikusa , Nagoya 464-8602 , Japan . Email: ;c CREST , Japan Science and Technology Agency (JST) , Nagoya University , Nagoya 464-8603 , Japan |
| Abstract: | 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. |
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