Highly enantioselective rhodium-catalyzed hydroboration of allylic phosphonates by pinacolborane affords chiral tertiary boronic esters. The β-borylated phosphonates are readily converted to chiral β- and γ-hydroxyphosphonates and aminophosphonates and to phosphonates bearing a quaternary carbon stereocenter. The utility of the latter is illustrated by the synthesis of (S)-(+)-bakuchiol methyl ether.
Journal of the American Chemical Society. 2017 May 3;139(17):6066-6069. doi: 10.1021/jacs.7b02324 Q115.62025
Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes
手性三级硼酸酯的合成：磷酸盐导向催化的三取代烯烃不对称氢硼化反应 翻译改进
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DOI: 10.1021/jacs.7b02324 PMID: 28414243
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