Chiral- Amine- Catalyzed Asymmetric Bromocyclization of Tryptamine Derivatives

被引：42

作者：

Cai, Quan ^{[1
]}

Yin, Qin ^{[1
]}

You, Shu-Li ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 3卷 / 04期

基金：

中国国家自然科学基金;

关键词：

bromocyclization; (DHQ)(2)PHAL; hexahydropyrro[2; 3]indoles; L-(-)-camphorsulfonic acid; tryptamine; CONCISE TOTAL-SYNTHESIS; HIGHLY EFFICIENT SYNTHESIS; ENANTIOSELECTIVE BROMOLACTONIZATION; PHOSPHORIC-ACID; TRYPTOPHAN; CYCLIZATION; ALKALOIDS; IODOLACTONIZATION; REARRANGEMENT; HALOGENATION;

D O I：

10.1002/ajoc.201300146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral hexahydropyrro[2,3]indole (HPI) units exist widely in natural and unnatural products with significant biological activities. The enantioselective synthesis of brominated hexahydropyrrolo[2,3-b]indole (HPI) subunits by asymmetric bromocyclization of tryptamine derivatives catalyzed by a chiral amine has been realized. In the presence of hydroquinine 1,4-phthalazinediyl diether ((DHQ)(2)PHAL, 20mol%) and L-(-)-camphorsulfonic acid (20mol%), enantioenriched brominated HPI derivatives were obtained from readily available substituted tryptamines in up to 99% yield and 73%ee.

引用

页码：408 / 411

页数：4

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