通过顺序有机催化迈克尔-多米诺迈克尔/Aldol 反应立体选择性合成螺-十氢吲哚酮衍生物。
Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction.
机构信息
Department of Chemistry, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
Department of Chemistry, University of Jyväskylä, 40014 Jyväskylä, Finland.
出版信息
J Org Chem. 2022 Aug 5;87(15):10454-10461. doi: 10.1021/acs.joc.2c01046. Epub 2022 Jul 25.
A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a highly atom-economical Michael-domino Michael/aldol reaction sequence was optimized, yielding variously functionalized spiro-decalin oxindoles with excellent stereoselectivity (>99:1 dr, up to 92% ee).
发展了一种高对映选择性的方法来合成含有五个连续手性中心的螺环多环氧吲哚，其中包括两个四取代的碳原子。在基于吡咯烷的有机催化剂和 DBU 进行的顺序有机催化作用下，优化了高原子经济性的迈克尔-达诺迈克尔/羟醛缩合反应序列，得到了各种功能化的螺[十氢萘-2,1'-吲哚]，具有极好的对映选择性（>99:1 dr，高达 92%ee）。
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