Periasamy, Mariappan ; Narsi Reddy, Meda ; Anwar, Shaik (2004) Synthesis and resolution of 1-(α-pyrrolidinylbenzyl)-2-naphthol and its application in the resolution of 2,2'-dihydroxy-1,1'-binaphthyl Tetrahedron: Asymmetry, 15 (11). pp. 1809-1812. ISSN 0957-4166
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...
Related URL: http://dx.doi.org/10.1016/j.tetasy.2004.04.030
Abstract
1-(α-Pyrrolidinylbenzyl)-2-naphthol 2 is easily prepared in 95% yield using benzaldehyde, 2-naphthol and pyrrolidine in ethanol at 78°C. It is resolved using inexpensive l-(+)-tartaric acid to obtain non-racemic samples that can be readily purified to enantiomeric purity through preparation of hydrogen bonded aggregates. The homochiral 1-(α-pyrrolidinylbenzyl)-2-naphthol 2 is useful in the resolution of racemic 2,2'-dihydroxy-1,1'-binaphthyl (BINOL) 3 via preparation of the corresponding diastereomeric borate complexes using B(OH)3.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 37275 |
| Deposited On: | 25 Apr 2011 08:07 |
| Last Modified: | 25 Apr 2011 08:07 |
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