Catalytic Enantioselective Synthesis of Axially Chiral Diarylmethylidene Indanones

被引:20
作者
Kumar, Prashant [1 ]
Shirke, Rajendra P. [1 ]
Yadav, Sonu [1 ]
Ramasastry, S. S., V [1 ]
机构
[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Organ Synth & Catalysis Lab, Manauli 140306, Punjab, India
关键词
MORITA-BAYLIS-HILLMAN; CROSS-COUPLING REACTIONS; ATROPOSELECTIVE SYNTHESIS; MEDICINAL CHEMISTRY; DERIVATIVES; REACTIVITY; COMPLEXES; MOLECULES; LIGANDS;
D O I
10.1021/acs.orglett.1c01671
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe the first atropselective Suzuki-Miyaura cross-coupling of beta-keto enol triflates to access axially chiral (Z)-diarylmethylidene indanones (DAIs). The chemical, physical, and biological properties of DAIs are unknown, despite their being structurally similar to arylidene indanones, primarily due to the lack of racemic or chiral methods. Through this work, we demonstrate a general and efficient protocol for the racemic as well as the atropselective synthesis of (Z)-DAIs. An unusual intramolecular Morita-Baylis-Hillman reaction is utilized for the Z-selective synthesis of beta-keto enol triflates.
引用
收藏
页码:4909 / 4914
页数:6
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