Catalytic asymmetric carbohydroxylation of alkenes by a tandem diboration/Suzuki cross-coupling/oxidation reaction
Catalytic asymmetric carbohydroxylation of alkenes by a tandem diboration/Suzuki cross-coupling/oxidation reaction
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DOI：
10.1021/ol036219a
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发表时间：
2004-01-08
期刊：
影响因子：
5.2
通讯作者：
Morken, JP
中科院分区：
文献类型：
--
作者：
Miller, SP;Morgan, JB;Morken, JP
手性非对称1，2-二硼加合物是通过催化对映选择性二硼化反应生成的。这些加合物的氧化以良好的产率提供1，2-二醇。或者，1，2-二硼化合物可以与芳基卤化物原位反应，其中较少受阻的C-B键参与交叉偶联。然后在反应后处理中氧化剩余的C-B键，从而允许在串联的一锅二硼化/Suzuki偶联/氧化顺序中进行烯烃的净不对称碳羟基化。
Chiral nonsymmetric 1,2-diboron adducts are generated by catalytic enantioselective diboration. Oxidation of these adducts provides 1,2-diols in good yield. Alternatively, 1,2-diboron compounds may be reacted, in situ, with aryl halides wherein the less hindered C-B bond participates in cross-coupling. The remaining C-B bond is then oxidized in the reaction workup thereby allowing for net asymmetric carbohydroxylation of alkenes in a tandem one-pot diboration/Suzuki coupling/oxidation sequence.