Organocatalyzed Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β,γ-Unsaturated α-Ketoesters: An Access to Chiral Indolin-3-ones with Two Adjacent Tertiary Stereogenic Centers

被引：22

作者：

Chen, Shanren ^{[1
]}

Wang, Youming ^{[1
]}

Zhou, Zhenghong ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Inst & State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 22期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; 1ST TOTAL-SYNTHESIS; 2-MONOSUBSTITUTED INDOLIN-3-ONES; STEREOCONTROLLED CONSTRUCTION; 2-SUBSTITUTED INDOLIN-3-ONES; ENANTIOSELECTIVE SYNTHESIS; INDOLE ALKALOIDS; MANNICH REACTION; DUOCARMYCIN-A; CATALYSIS;

D O I：

10.1021/acs.joc.6b02070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Michael addition of 1-acetylindolin-3-ones to beta,gamma-unsaturated a-keto esters was investigated for the synthesis of chiral indolin-3-ones with two adjacent tertiary stereogenic centers. Under the catalysis of a chiral bifunctional squaramide derived from L-tert-leucine, a wide range of 1-acetylindolin-3-ones and beta,gamma-unsaturated alpha-ketoesters were well-tolerated in this transformation to provide the corresponding novel densely functionalized chiral indolin-3-one derivatives in high yield with excellent diastereo- and enantioselectivity under mild reaction conditions.

引用

页码：11432 / 11438

页数：7

共 52 条

[21] NEW APPROACH TO 3-OXYGENATED CARBAZOLES - SYNTHESIS OF HYELLAZOLE AND 4-DEOXYCARBAZOMYCIN B
KAWASAKI, T
NONAKA, Y
AKAHANE, M
MAEDA, N
SAKAMOTO, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (15): : 1777 - 1781
[22] A short route to ''reverse-prenylated'' pyrrolo[2,3-b]indoles via tandem olefination and Claisen rearrangement of 2-(3,3-dimethylallyloxy)indol-3-ones: First total synthesis of flustramine C
Kawasaki, T
Terashima, R
Sakaguchi, K
Sekiguchi, H
Sakamoto, M
[J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7525 - 7528
[23] Organocatalyzed Asymmetric Aldol Reactions of Ketones and β,γ-Unsaturated α-Ketoesters and Phenylglyoxal Hydrates
Konda, Swapna
Guo, Qun-Sheng
Abe, Manabu
Huang, Huicai
Arman, Hadi
Zhao, John C-G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) : 806 - 815
[24] Proline-Catalyzed Enantioselective Synthesis of Aza-Quaternary Carbon Derivatives
Li, Liqi
Han, Manyi
Xiao, Mingxing
Xie, Zhixiang
[J]. SYNLETT, 2011, (12) : 1727 - 1730
[25] Isatisine a, a novel alkaloid with an unprecedented skeleton from leaves of isatis indigotica
Liu, Ji-Feng
Jiang, Zhi-Yong
Wang, Rui-Rui
Zheng, Yong-Tang
Chen, Ji-Jun
Zhang, Xue-Mei
Ma, Yun-Bao
[J]. ORGANIC LETTERS, 2007, 9 (21) : 4127 - 4129
[26] An asymmetric normal-electron-demand aza-Diels-Alder reaction via trienamine catalysis
Liu, Jing-Xin
Zhou, Qing-Qing
Deng, Jin-Gen
Chen, Ying-Chun
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (47) : 8175 - 8178
[27] Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin-3-ones Bearing Quaternary Stereocenters
Liu, Ren-Rong
Ye, Shi-Chun
Lu, Chuan-Jun
Zhuang, Gui-Lin
Gao, Jian-Rong
Jia, Yi-Xia
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (38) : 11205 - 11208
[28] The squaramide-catalyzed asymmetric Michael/cyclization tandem reaction for the synthesis of chiral trifluoromethylated hydroxyimino tetrahydrobenzofuranones
Liu, Wei
Lai, Xiaoyan
Zha, Gaofeng
Xu, Yan
Sun, Panpan
Xia, Tao
Shen, Yongcun
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (14) : 3603 - 3607
[29] Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to α,β-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones
Liu, Yao-Zong
Zhang, Jie
Xu, Peng-Fei
Luo, Yong-Chun
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) : 7551 - 7555
[30] Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β-Nitrostyrenes Catalyzed by Bifunctional Thioureas: A Simple Access to 2-Functionalized Indoles
Liu, Yao-Zong
Cheng, Rui-Ling
Xu, Peng-Fei
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) : 2884 - 2887

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