Journal
TETRAHEDRON LETTERS
Volume 80, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153324
Keywords
Bifunctional organocatalyst; Isothiouronium salt; Asymmetric direct aldol reaction; Aqueous condition
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Funding
- Basic Science Research Pro-gram through the National Research Foundation of Korea - Ministry of Education [2018R1D1A3B07040876, 2021R1I1A3A04037235]
- National Research Foundation of Korea [2018R1D1A3B07040876] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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The first chiral proline amide-isothiouronium based bifunctional organocatalyst was developed, showing high to quantitative yields in aldol products with excellent control performance of diastereoselectivities and enantioselectivity.
We developed the first chiral proline amide-isothiouronium based bifunctional organocatalyst, it was prepared by methylation of the corresponding thiourea. This asymmetric catalyst provides aldol products in high to quantitative yields while achieving excellent control performance of diastereoselectivities (anti/syn, up to 95:5 dr) and enantioselectivity (up to 99% ee) in the aldol reaction of various benzaldehydes with a cyclohexanone in water and formic acid. (c) 2021 Elsevier Ltd. All rights reserved.
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