Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 36, Issue 7, Pages 587-593Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201800135
Keywords
amination; asymmetric catalysis; nucleophilic substitution; chirality; organocatalysis
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Funding
- Shenzhen STIC [JCYJ20160229205441091]
- Hong Kong RGC [16304115, 16311616, 16302617]
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An organocatalytic approach for direct conversion of racemic diarylmethanols to valuable chiral diarylmethylamines is described. Different from the previously reported elegant borrowing hydrogen approach, the present process employs a distinct complementary formal S(N)1 strategy. This approach enjoys excellent enantioselectivity, mild conditions, broad scope, and easy product derivatization. Mechanistically, control experiments also provided important insights into some notable features, such as substrate kinetic resolution and reversibility as well as the critical role of the ortho- hydroxy group in the substrate.
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