4.8 Article

α-Alkylation of Chiral Sulfinimines for Constructing Quaternary Chiral Carbons by Introducing Removable Directing Groups

Journal

ORGANIC LETTERS
Volume 20, Issue 5, Pages 1350-1354

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00105

Keywords

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Funding

  1. National Natural Science Foundation of China (NSFC) [81703343]
  2. Natural Science Foundation of Tianjin - China [16JCQNJC13300]
  3. Fundamental Research Funds for the Central Universities
  4. Tianjin science and technology innovation system and the condition of platform construction plan [14TXSYJC00572]
  5. National Biomedical Special Project of International Innovation Park [I3ZCZDSY03300]
  6. National Natural Science Funds of China [81402973, 81703581]
  7. Tianjin Science and Technology Project [15PTGCCX00140, 10ZCKFSY07200, 10ZCKFSY08800, 13ZCZDSY03800, 13ZXCXSY13500, 13ZCZDSY03300]
  8. Innovation fund for technology based firms [12ZXCXSY06500]

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This study developed a facile and efficient synthetic strategy to construct quaternary chiral centers at the alpha-position of imines and ketones. High regioselectivity and diastereoselectivity were achieved through the synergetic effect of electron-withdrawing directing groups and N-tert-butyl sulfinamide as chiral auxiliaries. Either of them could be removed under the optimized conditions without any epimerization.

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