Organocatalyzed direct aldol condensation using l-proline and BINAM-prolinamides: regio-, diastereo-, and enantioselective controlled synthesis of 1,2-diols |
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| Affiliation: | 1. Institute of Chemical Research of Catalonia, Av. Països Catalans, 16, 43007 Tarragona, Spain;2. Department de Química Orgànica, Universitat de Barcelona, c/ Martí i Franquès 1-11, 08028 Barcelona, Spain;1. Medicinal Chemistry Laboratory, Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan;2. Center for Frontier Research in Medicinal Science, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan;3. Department of Bio-Science, Nagahama Institute of Bio-Science and Technology, Tamura-cho, Nagahama 526-0829, Japan;1. School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 13, Changmingshui Road, Zhongshan 528458, PR China;2. School of Pharmacy, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China |
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| Abstract: | Recoverable BINAM-prolinamide derivatives, as well as l-proline, give results complementary to antibodies when used as organocatalysts for aldol reactions between aldehydes and α-alkoxyacetones driving regioselectively to anti/syn-1,2-diols. The formation of the iso-regioisomer is suppressed using α-hydroxyacetone in DMSO at rt, achieving the corresponding anti-1,2-diol with ee’s up to 85%. For α-alkoxyacetones (methoxy, benzyloxy, and tert-butyldimethylsilyloxy), the highest regio- and diastereoselectivity is achieved using α-methoxyacetone in DMF at 0 °C; the enantiomeric excess for the anti-1,2-isomer being up to 98%. |
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