Journal
CHEMICAL SCIENCE
Volume 6, Issue 11, Pages 6086-6090Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc02170g
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Funding
- CREST-JST
- MEXT
- Program for Leading Graduate Schools Integrative Graduate Education and Research Program in Green Natural Sciences in Nagoya University
- JSPS
- National Institute of General Medical Sciences [R01 GM103855]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM103855] Funding Source: NIH RePORTER
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A metal-free stereoselective reductive coupling reaction between isatins and aldehydes is reported. The reaction relies on commercial diethyl phosphite (similar to(sic)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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