Enantioselective Construction of Spirooxindole-Fused Cyclopentanes

被引：14

作者：

Docekal, Vojtech ^{[1
]}

Vopalenska, Andrea ^{[1
]}

Merka, Pavel ^{[1
]}

Konecna, Klara ^{[2
]}

Jand'ourek, Ondrej ^{[2
]}

Pour, Milan ^{[3
]}

Cisarova, Ivana ^{[4
]}

Vesely, Jan ^{[1
]}

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, Prague 12843 2, Czech Republic

[2] Charles Univ Prague, Fac Pharm Hradec Kralove, Dept Biol & Med Sci, Hradec Kralove 50005, Czech Republic

[3] Charles Univ Prague, Fac Pharm Hradec Kralove, Dept Organ & Bioorgan Chem, Hradec Kralove 50005, Czech Republic

[4] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Prague 12843 2, Czech Republic

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 18期

关键词：

4 CONSECUTIVE STEREOCENTERS; MICHAEL/ALPHA-ALKYLATION REACTIONS; ORGANOCATALYTIC CASCADE REACTIONS; CATALYTIC ASYMMETRIC-SYNTHESIS; SPIROCYCLOPENTANE BIOXINDOLES; CONTIGUOUS STEREOCENTERS; ALPHA-ALKYLATION; DISCOVERY; OXINDOLES; DERIVATIVES;

D O I：

10.1021/acs.joc.1c01116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with alpha,beta-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.

引用

页码：12623 / 12643

页数：21

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