Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes |
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| Affiliation: | 1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany;2. Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan;3. Department of Chemistry, University of Pavia, Viale Taramelli, 10, 27100 Pavia, Italy;1. Department of Chemistry, Kazi Nazrul University, Asansol, 713340, India;2. Department of Chemistry, National Institute of Technology Durgapur, Durgapur, 713209, India;1. Chemical Kinomics Research Center, Korea Institute of Science and Technology, Wolsong-gil 5, Seongbuk-gu, Seoul, Republic of Korea;2. Department of Chemistry, Sogang University, Baekbeomno 35, Mapogu, Seoul, Republic of Korea;1. Key Laboratory of Functional Inorganic Material Chemistry (MOE) School of Chemistry and Materials Science Heilongjiang University No. 74, Xuefu Road, Nangang District, Harbin, 150080, PR China;2. College of Materials Science and Chemical Engineering Harbin Engineering University Harbin, 150001, PR China |
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| Abstract: | Starting either from benzoylformic acid or ethyl oxamate and enantiopure β-amino alcohols, several chiral α-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield. |
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