Enantioselective [2+2] cycloaddition of 1,2-dihydroquinolines with 3-olefinic oxindoles via Bronsted acid catalysis

被引：4

作者：

Biao Wang ^{[1
,2
,3
]}

Xiao Yan ^{[4
]}

Han Zhong ^{[1
,2
,3
]}

Qin, Ouyang ^{[4
]}

Xu Tian ^{[1
,2
,3
]}

机构：

[1] Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Peoples R China

[2] Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Peoples R China

[3] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Peoples R China

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

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 06期

关键词：

DIELS-ALDER REACTION; CYCLOBUTANE DERIVATIVES; ASYMMETRIC-SYNTHESIS; ENE REACTIONS; DESIGN; CONSTRUCTION; ACTIVATION; ALKENES; MODE;

D O I：

10.1039/d1qo01708j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mutually complementary regiodivergent Bronsted acid-catalyzed atom-economical [2 + 2] cycloaddition and ene reactions of 1,2-dihydroquinolines with 3-olefinic oxindoles are reported. In the presence of a chiral phosphoramide catalyst, the [2 + 2] cycloaddition affords products with four contiguous stereocenters in good to excellent yields (up to 95%) and with high stereoselectivities (up to >99% ee, >20 : 1 dr). Conversely, with a stronger Bronsted acid, the trifluoromethanesulfonic acid catalyst leads to ene reaction products in high yields (up to 77%). Furthermore, the mechanisms of the reactions are discussed based on control experiments and DFT calculations.

引用

页码：1621 / 1627

页数：7

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