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A long-necked flask equipped with a rubber septum was flame-dried and placed under argon atmosphere. To this a 0.66-1.99 M THF solution of LiAIH4 (filtered through dry Celite) was introduced via a syringe, and then at room temperature an alcohol in THF (2.00 M, 1 equiv) was added in a dropwise manner over a period of ca. 10 min with stirring. Subsequently a THF solution of optically pure binaphthol [(I?)- or (S)-1] (0.6 M, 1 equiv) was added dropwise, and the resulting mixture was stirred usually for an additional 30 min at room temperature and used for the asymmetric reduction. Notably the BINAL-H reagent 3 (R'O = simple alkoxyl) thus formed in THF was cloudy but a near-solution which contained only a very small amount of suspension. If a large quantity ofprecipitate separates out for some reason, one should repeat the preparation from the beginning. Optically active binaphthol may racemize to some extent upon exposure to strong acids or bases in protic media.14" Care should be exercised in its recovery in reusable form. Decolorization of optically active bi- naphthol by charcoal caused serious racemization¡£ ´ó¸ÅÒâ˼¶¼¶®£¬Ö÷ÒªÊDz»Ì«È·¶¨ÕâЩ¶«Î÷ÊÇÔõô¼Ó½øÈ¥£¬Ë³ÐòʲôµÄ¡£¡£¡£ |
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Áõ²Ó²ÓÀÃÑô¹â: ½ð±Ò+5, ·ÒëEPI+1, ¡ïÓаïÖú 2014-03-20 16:14:38
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