BINOL 衍生物催化的靛红的对映选择性烯丙基硼化反应：在（R）-chimonamidine 合成中的应用。
BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine.
机构信息
Univ Rennes, CNRS, ISCR - UMR 6226, F-35000 Rennes, France.
出版信息
Org Biomol Chem. 2020 Aug 12;18(31):6042-6046. doi: 10.1039/d0ob01386b.
PMID:32729604
Abstract
The asymmetric synthesis of the 3-allyl-3-hydroxyoxindole skeleton was accomplished in yields up to 99% via a metal-free and enantioselective allylation of isatins (90-96% ee) using BINOL derivatives as catalysts and an optimized allylboronate. This methodology was applied at a gram-scale to the synthesis of the natural product (R)-chimonamidine.
摘要
通过使用 BINOL 衍生物作为催化剂和优化的烯丙基硼酸酯，实现了高达 99%产率的通过无金属和对映选择性烯丙基化靛红（90-96%ee）的不对称合成 3-烯丙基-3-羟基氧化吲哚骨架。该方法在克级规模上应用于天然产物（R）- chimonamidine 的合成。
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