4.0 Article

Enantioselective intramolecular Morita-Baylis-Hillman reaction using chiral bifunctional phosphinothiourea as an organocatalyst

Journal

TETRAHEDRON-ASYMMETRY
Volume 21, Issue 8, Pages 903-908

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2010.04.061

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Funding

  1. National Natural Science Foundation of China [20772029]
  2. Program for New Century Excellent Talents in University [NCET-07-0286]
  3. Fundamental Research Funds for the Central Universities
  4. State Key Laboratory of Elemento-organic Chemistry

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Chiral cyclohexane-based phosphinothioureas were found to be efficient organocatalysts for the enantio-selective intramolecular Morita-Baylis-Hillman reaction of omega-formyl-enone. Among the solvents screened, t-BuOH was the best one which provided good yield and enantioselectivity. Moreover in the presence of 3 mol % of phosphinothiourea 2b, the desired products were obtained in good-to-excellent yields with up to 98% ee under mild reaction conditions. (C) 2010 Elsevier Ltd. All rights reserved.

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