Chlorine, an atom economical auxiliary for asymmetric aldol reactions
Chlorine, an atom economical auxiliary for asymmetric aldol reactions
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DOI：
10.1039/c3ob27462d
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发表时间：
2013-01-01
影响因子：
3.2
通讯作者：
Britton, Robert
中科院分区：
文献类型：
--
作者：
Halperin, Shira D.;Britton, Robert
已经开发出一种用于醛不对称反应的辅助策略，其中辅助剂本身不是手性的，而是通过有机催化α-氯化引入的单个氯原子。然后在通过自由基还原除去氯原子之前利用氯原子的立体定向影响。该策略在几种羟醛 (92-99% ee) 和天然产物 (+)-二氢yashabushiketol 和 (+)-solistatin 的合成中得到了证明。
An auxiliary strategy has been developed for asymmetric reactions of aldehydes in which the auxiliary itself is not chiral, but a single chlorine atom introduced via organocatalytic alpha-chlorination. The stereo-directing influence of the chlorine atom is then exploited prior to its removal by radical reduction. This strategy is demonstrated in the synthesis of several aldols (92-99% ee) and the natural products (+)-dihydroyashabushiketol and (+)-solistatin.