Organocatalytic Stereoselective Mannich Reaction of 3-Substituted Oxindoles
- 19 July 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (16) , 3583-3586
- https://doi.org/10.1021/ol801351j
Abstract
The asymmetric Mannich reaction of 3-substituted oxindoles and N-Boc imines was investigated for the first time, employing bifunctional thiourea-tertiary amine organocatalysts based on DPEN scaffold. The novel transformations exhibited high diastereoselectivities, and the Mannich adducts bearing adjacent quaternary and tertiary chiral centers were generally obtained in good to excellent enantioselectivities (up to 95% ee).Keywords
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