Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 12, Pages 4650-4653Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9006688
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Funding
- National Natural Science Foundation of China
- Chinese Academy of Sciences
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The modified cinchona alkaloid-catalyzed direct Mannich-type reaction of N-unprotected 2-oxindoles with N-Ts-imine was developed to afford anti-3,3-disubstituted 2-oxindoles with vicinal chiral quaternary and tertiary carbon centers in yields up to 90% with excellent diastereoselectivities (antil syn up to 95:5) and good enantioselectivies (up to 89% ee). A transition model for the anti-diastereo- and enantioselectivity of the reaction was proposed.
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