Privilege-Structure-Oriented Three-ComPonent Asymmetric Aminomethylation: Assembly of Chiral 3-Aminomethyl Indolones

被引：24

作者：

Kang, Zhenghui ^{[1
]}

Zhang, Dan ^{[1
]}

Xu, Xinfang ^{[1
]}

Hu, Wenhao ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab Chiral Mol & Drug Discover, Guangzhou 510006, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 24期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; C-H FUNCTIONALIZATION; BRONSTED ACID; COOPERATIVE CATALYSIS; DIAZO-COMPOUNDS; CONSTRUCTION; CARBENE; YLIDES; EPIDITHIODIOXOPIPERAZINES; SPIROINDOLONES;

D O I：

10.1021/acs.orglett.9b03787

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric aminomethylation reaction of 3-diazooxindoles with electronic-rich arenes and N,0-acetals cooperatively catalyzed by achiral dirhodium complex and chiral phosphoric acid is reported. The reaction provides a novel method for the facile synthesis of chiral 3-aminomethyl oxindoles with an all -carbon quaternary center in good yields (82-98%) with high to excellent enantioselectivities (up to 97% ee). The transformation proceeds through a convergent addition of a reactive zwitterionic intermediate with a chiral methylene iminium generated in situ via asymmetric counteranion -directed catalysis (ACDC). This work represents the first asymmetric aminomethylation method of mixed 3,3'-bisindoles with structural diversity.

引用

页码：9878 / 9883

页数：6

共 5 条

[1] Asymmetric Three-Component Propargyloxylation for Direct Assembly of Polyfunctionalized Chiral Succinate Derivatives
Lv, Xinxin
Liu, Shuhao
Zhou, Su
Dong, Guizhi
Xing, Dong
Xu, Xinfang
Hu, Wenhao
CCS CHEMISTRY, 2021, 3 (07): : 1903 - 1912
[2] Asymmetric Three-Component Propargyloxylation for Direct Assembly of Polyfunctionalized Chiral Succinate Derivatives (vol 3, pg 1903, 2021)
Lv, X.
CCS CHEMISTRY, 2022, 4 (12): : 3900 - 3900
[3] Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis
1600, American Chemical Society (125):
[4] Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis
Chen, C
Li, XD
Schreiber, SL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) : 10174 - 10175
[5] Chiral α-substituted allylboronates in a one-pot three-component asymmetric allylic alkylation/carbonyl allylation reaction sequence - Applications to the syntheses of (+)-(3R, 5R)-3-hydroxy-5-decanolide and (-)-massoialactone
Carosi, Lisa
Hall, Dennis G.
CANADIAN JOURNAL OF CHEMISTRY, 2009, 87 (05) : 650 - 661

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