A facial chemoenzymatic method for the preparation of chiral 1,2-dihydroxy-3,3,3,-trifluoropropanephosphonates |
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| Authors: | Chengye Yuan Jinfeng Li Wenchi Zhang |
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| Affiliation: | State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng-Lin Lu, Shanghai 200032, China |
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| Abstract: | A convenient and effective method for the preparation of chiral trifluoromethylated 1,2-dihydroxypropanephosphonates based on a chemoenzymatic approach was described. Ethyl trifluoromethylacetate was reacted with anion of methylphosphonate to give 2-oxo-3,3,3-trifluoropropanephosphonate and its hydrates, 2,2-dihydroxy-3,3,3-trifluoropropanephosphonates, which are reduced with sodium boronhydride affording 2-hydroxy-3,3,3-trifluoropropanephosphonates. The product thus obtained was then transferred to corresponding 1,2-vinyl-3,3,3-trifluoropropanephosphonate and followed by 1,2-dihydroxylation via potassium permanganate treatment. Enzymatic kinetic resolution of the resultant racemate by CALB or IM provided optically active 1,2-dihydroxy-3,3,3-trifluoropropanephosphonate with satisfactory chemical and enantiomeric yield. |
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| Keywords: | Chemoenzymatic method Trifluoromethylated hydroxyphosphonate Hydroxyphosphonate Kinetic resolution |
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