Remote Central-to-Axial Chirality Conversion: Direct Atroposelective Ester to Biaryl Transformation
Remote Central-to-Axial Chirality Conversion: Direct Atroposelective Ester to Biaryl Transformation
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DOI：
10.1002/anie.201803472
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发表时间：
2018-06-11
影响因子：
16.6
通讯作者：
Sparr, Christof
中科院分区：
文献类型：
--
作者：
Link, Achim;Sparr, Christof
提出了一种通过编码和瞬态立体中心同时平面化实现远端中心到轴向手性转换的方法。基于手性1,5-双功能有机烷氧镁试剂在广泛的芳基酯底物上的非对映选择性双加成，通过原位还原直接获得轴向手性双芳基。作为有价值的手性双芳基阴离子替代物的各种结构独特的atropisomer biaryl硅烷可以一步获得，其e.r值高达98:2。
A strategy for the remote central-to-axial chirality conversion by simultaneous planarization of an encoding and a transient stereocenter is presented. Based on a diastereoselective double addition of a chiral 1,5-bifunctional organomagnesium alkoxide reagent to a broad range of aryl ester substrates, axially chiral biaryls are directly obtained upon in situ reduction. Various structurally distinct atropisomeric biaryl silanes that serve as valuable chiral biaryl anion surrogates are accessible in one step with e.r.values of up to 98:2.