Synthesis of 3-Indolylglycine Derivatives via Dinuclear Zinc Catalytic Asymmetric Friedel-Crafts Alkylation Reaction

被引:43
作者
Wang, Xin-Wei [1 ]
Hua, Yuan-Zhao [1 ]
Wang, Min-Can [1 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, 75 Daxue St, Zhengzhou 450052, Henan Province, Peoples R China
关键词
HIGHLY DIASTEREOSELECTIVE SYNTHESIS; AMINO-ACID DERIVATIVES; 1ST TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIHYDROHAMACANTHIN-A; ORGANOZINC REAGENTS; BISINDOLE ALKALOIDS; GLYOXYLATE IMINES; CYCLOHEXENE OXIDE; MANNICH REACTIONS;
D O I
10.1021/acs.joc.6b01805
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct asymmetric Friedel-Crafts (F-C) alkylation reaction between a wide range of indoles and ethyl 2-(4-methoxyphenylimino)acetate catalyzed by Trost's dinuclear complex is reported. A series of 3-indolylglycine derivatives were synthesized in enantioselectivity of up to >99% enantiomeric excess (ee) using 10 mol% catalyst loading under mild conditions. This atom economic reaction could be run on a gram scale without impacting its enantioselectivity. The absolute stereochemistry of catalytic products was determined by correlation with a known configuration compound. A possible mechanism was proposed for the asymmetric induction.
引用
收藏
页码:9227 / 9234
页数:8
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