4.6 Article

An enantioselective organocatalyzed aza-Morita-Baylis-Hillman reaction of isatin-derived ketimines with acrolein

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY
卷 13, 期 34, 页码 9022-9028

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob00874c

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资金

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
  2. CREST project of the Japan Science and Technology Corporation (JST)
  3. Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) of JST
  4. JSPS
  5. Grants-in-Aid for Scientific Research [26105747, 25253002, 26105737] Funding Source: KAKEN

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A highly enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with acrolein was established using beta-isocupreidine (beta-ICD) or alpha-isocupreine (alpha-ICPN) as a chiral acid-base organocatalyst. The present protocol readily furnished (S) or (R)-aza-MBH adducts with a chiral tetra-substituted carbon stereogenic center in up to 98% ee.

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