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Asymmetric hydroboration of [E]- and [Z]-2-methoxy-2-butenes. Synthesis of (−)-[2R,3R]-butane-2,3-diol in >97% ee |
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| Authors: | Dhanabalan Murali Bakthan Singaram Herbert C Brown |
| Institution: | a H.C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA b Department of Chemistry and Biochemistry, University of California, Santa Cruz, CA 95064, USA |
| Abstract: | Asymmetric hydroboration of E]- and Z]-2-methoxy-2-butene, using (−)-diisopinocampheylborane at −25°C in THF solvent, followed by oxidation using H2O2/NaOH, gave (−)-2R,3R]- and (+)-2R,3S]-3-methoxy-2-butanols in >97 and 90% ee, respectively. (−)-2R,3R]-3-Methoxy-2-butanol was converted to (−)-2R,3R]-butane-2,3-diol (>97% ee, in an overall yield of 65%). |
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