Department of Chemistry, University of Nebraska-Lincoln , Lincoln, Nebraska 68588-0304, United States.
J Am Chem Soc. 2017 May 3;139(17):6066-6069. doi: 10.1021/jacs.7b02324. Epub 2017 Apr 20.
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.
手性膦酸酯的高对映选择性铑催化烯丙基膦酸酯的硼氢化反应由频哪醇硼烷提供。β-硼化膦酸酯容易转化为手性β-和γ-羟基膦酸酯和氨基膦酸酯以及带有季碳立体中心的膦酸酯。后者的用途通过（S）-（+）-补骨脂酚甲醚的合成得到说明。
