Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 22, Pages 6492-6496Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600453
Keywords
[3+2] cycloaddition; acyclic ketimines; amino acids; phosphine catalysts; spirooxindoles
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Funding
- Zhejiang University of Science Technology
- National Natural Science Foundation of China [21402177]
- Singapore A*STAR SERC Public Sector Research Funding (PSF) [R-143-000-618-305]
- National University of Singapore [R-143-000-599-112]
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Phosphine-catalyzed enantioselective annulation reactions involving ketimines are a daunting synthetic challenge owing to the intrinsic low reactivity of ketimine substrates. A highly enantioselective [3+2] cycloaddition reaction that makes use of isatin-derived ketimines as reaction partners was developed. Notably, both simple and gamma-substituted allenoates could be utilized, and various 3,2'-pyrrolidinyl spirooxindoles with a tetrasubstituted stereocenter were obtained in excellent yields and with nearly perfect enantioselectivity (>98% ee in all cases).
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