Journal
ORGANIC LETTERS
Volume 17, Issue 8, Pages 2006-2009Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00749
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Funding
- Japan Society for the Promotion of Science (JSPS)
- Global COE Program, The University of Tokyo, MEXT, Japan
- Japan Science Technology Agency (JST)
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Chiral Ca-catalyzed asymmetric addition reactions of 3-substituted oxindoles with N-Boc-imines afford 3-tetrasubstituted oxindole derivatives bearing adjacent quaternary and tertiary chiral centers, which are key structures for biological activities. Ubiquitous and nontoxic Ca catalysts (1-10 mol %) work well in this reaction, and high yields (up to >99%) and selectivities (up to >99% ee) of the products with wide substrate scope have been attained. The structures of the chiral Ca catalysts and intermediary Ca enolates are also discussed.
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