4.7 Article

Direct asymmetric aldol addition-isomerization of α,β-unsaturated γ-butyrolactam with aryl α-ketoesters: synthesis of MBH-type products

Journal

CHEMICAL COMMUNICATIONS
Volume 49, Issue 32, Pages 3300-3302

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc40717a

Keywords

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Funding

  1. National Natural Science Foundation of China [91213302, 20932003, 21272102]
  2. Key National S&T Program Major New Drug Development'' of the Ministry of Science and Technology of China [2012ZX09504001-003]
  3. Program for Changjiang Scholars and Innovative Research Team in University [PCSIRT: IRT1137]

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A highly efficient direct asymmetric aldol addition-isomerization reaction at the alpha-position of alpha,beta-unsaturated gamma-butyrolactam and aryl alpha-ketoesters by using a bifunctional thiourea catalyst was achieved. Morita-Baylis-Hillman type adducts containing a quaternary stereocenter can be obtained in high yields and with excellent enantioselectivities (up to 99% ee).

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