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
收藏
页码：408 / 411
页数：4
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