Heteroatom-Directed Acylation of Secondary Alcohols To Assign Absolute Configuration.
| Autor: | Burns AS; Department of Chemistry, 1102 Natural Sciences II, University of California at Irvine , Irvine, California 92697, United States., Ross CC; Department of Chemistry, 1102 Natural Sciences II, University of California at Irvine , Irvine, California 92697, United States., Rychnovsky SD; Department of Chemistry, 1102 Natural Sciences II, University of California at Irvine , Irvine, California 92697, United States. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2018 Mar 02; Vol. 83 (5), pp. 2504-2515. Date of Electronic Publication: 2018 Feb 09. |
| DOI: | 10.1021/acs.joc.7b03156 |
| Abstrakt: | Birman's HBTM catalyst is effective for the enantioselective acylation and kinetic resolution of benzylic secondary alcohols. The enantioselective acylation has now been extended to secondary alcohols bearing electron-withdrawing groups such as halides and other heteroatoms. The level of selectivity is modest to good and is sufficient for determining configuration using the competing enantioselective conversion method. A mathematical analysis identifies conditions for achieving maximum differences in conversion and, consequently, assigning configuration with greater confidence. The new method is effective for halohydrins and secondary-tertiary 1,2-diols and was used to confirm the configuration of two inoterpene natural products. |
| Databáze: | MEDLINE |
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