通过靛红衍生的 - 醌甲醚实现生物相关的 3,3- 二羟基苯并恶唑的有机催化不对称合成。
Organocatalytic Asymmetric Synthesis of Biologically Relevant 3,3- Dihydroxyphenyloxindoles via -Quinone Methides Derived from Isatins.
机构信息
College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, People's Republic of China.
出版信息
J Org Chem. 2021 Apr 16;86(8):5489-5498. doi: 10.1021/acs.joc.0c03004. Epub 2021 Mar 29.
PMID:33779183
Abstract
The first asymmetric synthetic approach to biologically relevant 3,3-diphenyloloxindoles was developed using -quinone methides derived from isatins and phenols. Chiral phosphoric acid efficiently catalyzed the reaction and delivered 3,3-diphenyloloxindoles under mild conditions with up to an equivalent yield and excellent enantioselectivity (up to >99% ee). The chirality was maintained in further synthesis.
摘要
首次采用 - 醌甲醚，由色酮和酚衍生而来，发展了一种具有生物相关意义的 3,3-二苯基氧吲哚的不对称合成方法。手性磷酸能够高效地催化该反应，在温和的条件下以高达当量的产率和优异的对映选择性（高达 >99%ee）得到 3,3-二苯基氧吲哚。在进一步的合成中，手性得到了保持。
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