Novel fluorous prolinol as a pre-catalyst for catalytic asymmetric borane reduction of various ketones |
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Authors: | Sakiko Goushi Masaya Ohta Keisuke Hatano Masaki Matsui |
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Institution: | Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan |
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Abstract: | Novel prolinol carrying two perfluorohexylethyl groups at the α-position was prepared from l-proline as a starting chiral substrate. Catalytic asymmetric reduction of various ketones, including mono-, di-, and trifluoromethylated acetophenones, using fluorous oxazaborolidines derived from fluorous prolinol afforded the corresponding alcohols in good to excellent yields and with high enantioselectivities (up to 93.2% ee). The fluorous prolinol was recovered without any fluorous solvents or silica gel by simply cooling the organic phase and filtration. |
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