Organocatalytic enantioselective decarboxylative Michael addition of β-ketoacids to α,β-unsaturated ketones

被引：70

作者：

Kang, Young Ku ^{[1
]}

Lee, Hyun Joo ^{[1
]}

Moon, Hyoung Wook ^{[1
]}

Kim, Dae Young ^{[1
]}

机构：

[1] Soonchunhyang Univ, Dept Chem, Asan 336745, Chungnam, South Korea

来源：

RSC ADVANCES | 2013年 / 3卷 / 05期

关键词：

MANNICH-TYPE REACTIONS; ASYMMETRIC CONJUGATE ADDITION; C-3-SYMMETRIC CHIRAL TRISIMIDAZOLINE; ELECTROPHILIC ALPHA-AMINATION; FRIEDEL-CRAFTS ALKYLATION; ACID HALF-THIOESTERS; QUATERNARY STEREOCENTERS; 1,3-DICARBONYL COMPOUNDS; TERTIARY STEREOCENTERS; POLYKETIDE SYNTHASES;

D O I：

10.1039/c2ra21945j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective decarboxylative Michael addition reactions promoted by chiral primary amine organocatalysts have been developed, allowing the facile synthesis of the corresponding chiral 1,5-diketones with excellent enantioselectivity (up to 97% ee). The method reported represents a valuable approach of utilizing beta-ketoacids as synthetic equivalents of aryl methyl ketones.

引用

页码：1332 / 1335

页数：4

共 50 条

[1] Enantioselective Organocatalytic Michael Addition to Unsaturated Indolyl Ketones
Trubitson, Dmitri
Martonova, Jevgenija
Kudrjasova, Marina
Erkman, Kristin
Jarving, Ivar
Kanger, Tonis
ORGANIC LETTERS, 2021, 23 (05) : 1820 - 1824
[2] Enantioselective Organocatalytic Michael Addition of Malonates to α,β-Unsaturated Ketones
Li, Pengfei
Wen, Shigang
Yu, Feng
Liu, Qiaoxia
Li, Wenjun
Wang, Yongcan
Liang, Xinmiao
Ye, Jinxing
ORGANIC LETTERS, 2009, 11 (03) : 753 - 756
[3] Highly Enantioselective Organocatalytic Sulfa-Michael Addition to α,β-Unsaturated Ketones
Rana, Nirmal K.
Selvakumar, Sermadurai
Singh, Vinod K.
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (06): : 2089 - 2091
[4] Organocatalytic Enantioselective Aza-Michael Addition of Purine Bases to α,β-Unsaturated Ketones
Wu, Hao
Tian, Zhiqing
Zhang, Lili
Huang, Yaodong
Wang, Yongmei
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2977 - 2984
[5] Enantioselective Organocatalytic Michael Addition of Ketones to Alkylidene Malonates
Syu, Siang-En
Huang, Chan-Hui
Chen, Ko-Wei
Lee, Chia-Jui
Das, Utpal
Jang, Yeong-Jiunn
Lin, Wenwei
CHIRALITY, 2012, 24 (08) : 600 - 605
[6] ENANTIOSELECTIVE ORGANOCATALYTIC MICHAEL ADDITION OF ALIPHATIC KETONES TO NITRODIENES
He, Tianxiong
Wu, Xin-Yan
SYNTHETIC COMMUNICATIONS, 2012, 42 (05) : 667 - 677
[7] Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes
Wu, Shanchao
Li, Yu
Zhang, Yongqiang
Fang, Kun
Dong, Guoqiang
Liu, Na
Miao, Zhenyuan
Yao, Jianzhong
Wang, Wei
Zhang, Wannian
Sheng, Chunquan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (16) : 3926 - 3933
[8] Enantioselective organocatalytic phospha-Michael reaction of α,β-unsaturated ketones
Wen, Shigang
Li, Pengfei
Wu, Haibo
Yu, Feng
Liang, Xinmiao
Ye, Jinxing
CHEMICAL COMMUNICATIONS, 2010, 46 (26) : 4806 - 4808
[9] Organocatalytic Enantioselective Michael Addition of 4-Hydroxycoumarin to α,β-Unsaturated Ketones: A Simple Synthesis of Warfarin
Dong, Zhenhua
Wang, Lijia
Chen, Xiaohong
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (30) : 5192 - 5197
[10] Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins
Wei, Yi
Guo, Ran
Dang, Yanfeng
Nie, Jing
Ma, Jun-An
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (17) : 2721 - 2726

← 1 2 3 4 5 →