Highly enantioselective addition of in situ prepared arylzinc to aldehydes catalyzed by a series of atropisomeric binaphthyl-derived amino alcohols |
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Authors: | Lu Gui Kwong Fuk Yee Ruan Ji-Wu Li Yue-Ming Chan Albert S C |
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Affiliation: | Open Laboratory of Chirotechnology of the Institute of Molecular, Technology for Drug Discovery and Synthesis State Key Laboratory of Chinese Medicine and Molecular Pharmacology (Shenzhen), Kowloon, Hong Kong, China. |
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Abstract: | The direct addition of in situ prepared arylzinc to aldehydes with chiral binaphthyl-derived amino alcohols as catalysts can afford optically active diarylmethanols in high yields and with excellent enantioselectivities (up to 99 % ee, ee = enantiomeric excess). By using a single catalyst, both enantiomers of many pharmaceutically interesting diarylmethanols can be obtained by the proper combination of various arylzinc reagents with different aldehydes; this catalytic system also works well for the phenylation of aliphatic aldehydes to give up to 96 % ee. |
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Keywords: | amino alcohols arylation arylzinc binaphthyl enantioselectivity |
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