Asymmetric Diels-Alder Reaction of 3-Vinylindoles and Nitroolefins Promoted by Multiple Hydrogen Bonds

被引：24

作者：

Yang, Xi ^{[1
,2
]}

Zhou, Yu-Hao ^{[1
,2
]}

Yang, Han ^{[1
,2
]}

Wang, Shan-Shan ^{[1
,2
]}

Ouyang, Qin ^{[3
]}

Luo, Qun-Li ^{[1
,2
]}

Guo, Qi-Xiang ^{[1
,2
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

[2] Southwest Univ, Sch Chem & Chem Engn, Chongqing Key Lab Soft Matter Mat Chem & Funct Mf, Chongqing 400715, Peoples R China

[3] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 04期

关键词：

MICHAEL ADDITION; ALKALOIDS; DONORS; 3-INDOLYLMETHANOLS; ORGANOCATALYSTS; CONSTRUCTION; CYCLIZATION; ACCESS;

D O I：

10.1021/acs.orglett.9b00104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric Diels-Alder reaction of 3-vinylindole and nitroolefin is described. In the promotion of organocatalyst 3j, structurally diverse 1-nitro-hydrocarbazoles are produced in moderate-to-good yields and high-to-excellent enantioselectivities. All of these products are obtained as a single diastereoisomer. The 1-nitro-hydrocarbazole compounds can be converted into 1-amino-hydrocarbazole derivatives and structurally complex ring fused indoles enantioseletively. Possible transition states were investigated by control experiments and DFT calculations.

引用

页码：1161 / 1164

页数：4

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