Anomalies in the asymmetric hydroboration of olefins with the adduct of (+)-α-pinene and BH3 · THF |
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Authors: | Arun K Mandal Nung Min Yoon |
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Affiliation: | Richard B. Wetherill Laboratory, Purdue University, West Lafayette, Indiana 47907 U.S.A. |
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Abstract: | The hydroboration of cis-2-butene and cis-3-hexene with pure diisopinocampheylborane (IPC2BH) and monoisopinocampheylborane (IPCBH2), both prepared from (+)-α-pinene, were studied. In contrast to IPC2BH, which yielded R-(?)-2-butanol and R-(?)-3-hexanol in 98.4 and 94.5% optical purities, IPCBH2 yielded S-(+)-2-butanol and S-(+)-3-hexanol in 23.6 and 19.7% optical purifies respectively. PMR examination of the methanolyzed products were utilized to establish the species present in the freshly prepared and aged adduct from (+)-α-pinene and BH3 · THF. The results confirm the interpretation previously advanced for the major differences realized in asymmetric hydroboration with the fresh and aged adducts. |
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