Journal
CHEMICAL SCIENCE
Volume 1, Issue 5, Pages 590-595Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0sc00385a
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Funding
- National Natural Science Foundation of China [20732003]
- PCSIRT [IRT0846]
- National Basic Research Program of China (973 Program) [2010CB833300]
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Highly enantioselective synthesis of 1,3-bis(hydroxymethyl)-2-oxindoles was established through chiral Nd-III-N,N'-dioxide in up to 93% yield and >99% cc under mild conditions. The key features of this approach include using cheap and readily available formalin as a hydroxymethylation Cl unit and unprotected 3-substituted-2-oxindoles as nucleophiles directly. The initial C-aldol product from 3-substituted-2-oxindole was converted to the corresponding 1,3-bis(hydroxymethyl)-2-oxindole derivative immediately under the reaction conditions. Moreover, the catalyst was water-tolerant, and ligand and Nd(OTf)(3) could be easily recovered and reused with no loss in catalytic activity and enantioselectivity. The synthetic utility of this methodology was accomplished with the synthesis of key intermediates of physostigmine and coerulescine.
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