3-氨基氧化吲哚席夫碱作为手性辅基用于双功能金鸡纳碱催化的迈克尔/环化反应对映选择性制备螺[氧化吲哚-3,2'-吡咯]
3-Amino Oxindole Schiff Base as Synthon for Enantioselective Preparation of Spiro[oxindol-3,2'-pyrrol] from a Michael/Cyclization Reaction Catalyzed by a Bifunctional Cinchona.
机构信息
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences Chengdu 610041, China.
University of Chinese Academy of Sciences, Beijing 100049, China.
出版信息
Org Lett. 2021 Mar 19;23(6):2227-2231. doi: 10.1021/acs.orglett.1c00370. Epub 2021 Mar 3.
A new and crucial synthon of 3-((diphenylmethylene)-amino)-oxindole was designed and synthesized, for which an organocatalytic and enantioselective Michael/cyclization reaction with a terminal vinyl ketone catalyzed by a cinchona base was disclosed. A wide variety (28 examples) of almost all new chiral spiro[oxindol-3,2'-pyrrols] were prepared in excellent yields (up to 99%) with excellent enantioselectivities (95-99% ee), of which a typical chiral spiro product was further reduced to chiral spiro[oxindole-3,2'-pyrrolidine].
设计并合成了一种新的、关键的 3-((二苯基亚甲基)-氨基)-氧吲哚合成子，其中揭示了一种金鸡纳碱催化的末端乙烯基酮的有机催化和对映选择性迈克尔/环化反应。通过该反应，可以以优异的收率（高达 99%）和对映选择性（95-99%ee）制备多种（28 个实例）几乎全新的手性螺[氧吲哚-3,2'-吡咯]。其中，一个典型的手性螺产物进一步还原为手性螺[氧吲哚-3,2'-吡咯烷]。
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