AI Article Synopsis
- The study presents a method using rhodium catalysts to create chiral tertiary boronic esters from allylic phosphonates through hydroboration with pinacolborane.
- These β-borylated phosphonates can be easily transformed into various chiral hydroxyphosphonates and aminophosphonates, as well as phosphonates with quaternary carbon stereocenters.
- The practical application of this method is demonstrated by synthesizing (S)-(+)-bakuchiol methyl ether, showcasing its relevance in producing complex organic molecules.
Article Abstract
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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5423446 | PMC |
| http://dx.doi.org/10.1021/jacs.7b02324 | DOI Listing |
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