Reagent-Controlled Regiodivergent Resolution of Unsymmetrical Oxabicyclic Alkenes Using a Cationic Rhodium Catalyst

Reagent-Controlled Regiodivergent Resolution of Unsymmetrical Oxabicyclic Alkenes Using a Cationic Rhodium Catalyst
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DOI:
10.1021/ja807942m
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发表时间:
2009-01-21
影响因子:
15
通讯作者:
Lautens, Mark
Lautens, Mark
中科院分区:
化学1区
文献类型:
--
作者:
Webster, Robert;Boeing, Christian;Lautens, Mark

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Rh(I)催化的regiodivergent除了杂原子亲核试剂外消旋oxabicyclic烯烃产生良好的产率的regiosomeric产品,每个在高ee. Powerful试剂控制证明,作为基板的固有反应性是完全由手性催化剂络合物,这是需要使用阳离子Rh(I)。该方法提供了从简单的起始原料以高对映选择性快速获得多种1,2-二氢萘产物。
A Rh(I) catalyzed regiodivergent addition of heteroatom nucleophiles to racemic oxabicyclic alkenes produces good yields of regioisomeric products each in high ee. Powerful reagent control is demonstrated, as the inherent reactivity of the substrate is completely dominated by the chiral catalyst complex, which is shown to require the use of cationic Rh(I). The process affords rapid access to multiple 1,2-dihydronapthalene products in high enantioselectivity from simple starting materials.