Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 13, Issue 17, Pages 2440-2444Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201800569
Keywords
amino acids; chirality; organocatalysis; quinone methides; synthetic methods
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Funding
- Shenzhen Science and Technology Innovation Committee [JCYJ20160229205441091]
- Hong Kong RGC [16304115, 16302617, 16311616]
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An organocatalytic intermolecular C-C bond formation process leading to the efficient synthesis of chiral ,-diaryl--amino acid derivatives is described. In the presence of a suitable chiral phosphoric acid catalyst, a range of para-hydroxybenzyl alcohols serve as efficient precursors to para-quinone methides and then react with azlactones in 1,6-conjugate addition reactions. The asymmetric control has been carefully optimized together with diastereocontrol enabled by identification of the reversible feature of the C-C bond formation and subsequent inhibition by protection of the free hydroxy group in one pot. Compared with previous approaches, including those with pre-synthesized para-quinone methides, this protocol provides an alternative and complementary step- and pot-economical approach for the synthesis of chiral ,-diaryl--amino acid derivatives.
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