Catalytic enantioselective ene-type reactions of vinylogous hydrazone: construction of α-methylene-γ-butyrolactone derivatives

被引：19

作者：

Zhang, Hang ^{[1
]}

Yao, Qian ^{[1
]}

Cao, Weidi ^{[1
]}

Ge, Shulin ^{[1
]}

Xu, Jinxiu ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 88期

关键词：

STEREOCONTROLLED SYNTHESIS; CARBONYL-COMPOUNDS; BIS-HYDRAZONES; N; N-DIMETHYLHYDRAZONES; FORMALDEHYDE; LIGANDS; N-DIALKYLHYDRAZONES; CYCLOADDITION; ALDEHYDES; REAGENTS;

D O I：

10.1039/c8cc07567k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic asymmetric ene-type reactions of vinylogous hydrazone were accomplished by using chiral N,N-dioxide-metal salt complexes as catalysts. A wide range of electrophiles, including isatins, -ketoester, imines, and aldehydes reacted with (E)-2-methyl-N-(piperidin-1-yl)prop-2-en-1-imine efficiently, affording the corresponding homoallylic alcohols and amines in high yields (up to 99%) with excellent ee values (up to 99%). The methodology provided a convenient way to synthesize bioactive chiral -methylene--butyrolactone derivatives.

引用

页码：12511 / 12514

页数：4

共 12 条

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Zhang, Hang
Liu, Xiaohua
Feng, Xiaoming
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[2] Advancements in Catalytic Asymmetric Intermolecular Ene-Type Reactions
Liu, Xiaohua
Zheng, Ke
Feng, Xiaoming
SYNTHESIS-STUTTGART, 2014, 46 (17): : 2241 - 2257
[3] Catalytic Enantioselective Amide Allylation of Isatins and Its Application in the Synthesis of 2-Oxindole Derivatives Spiro-Fused to the α-Methylene-γ-Butyrolactone Functionality
Takahashi, Masaki
Murata, Yusuke
Yagishita, Fumitoshi
Sakamoto, Masami
Sengoku, Tetsuya
Yoda, Hidemi
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (35) : 11091 - 11100
[4] Possible Intervention of Prototropic and Silatropic Ene-type Mechanisms in Asymmetric Catalytic Mukaiyama Aldol Reactions
Honda, Kazuya
Mikami, Koichi
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (01) : 34 - 40
[5] Advancements in Catalytic Asymmetric Intermolecular Ene-Type Reactions (vol 46, pg 2241, 2014)
Liu, Xiaohua
Zheng, Ke
Feng, Xiaoming
SYNTHESIS-STUTTGART, 2014, 46 (19): : 2682 - 2682
[6] Gold Carbenes from Substituted Propargyl Acetates: Intramolecular Ene-type Reactions to 2-Acetoxynaphthalene Derivatives
Oh, Chang Ho
Kim, Ji Hee
Piao, Lanhua
Yu, Jin
Kim, So Young
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (32) : 10501 - 10505
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Drury, WJ
Ferraris, D
Cox, C
Young, B
Lectka, T
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) : 11006 - 11007
[8] HIGH ASYMMETRIC INDUCTION IN LEWIS ACID-PROMOTED INTRAMOLECULAR ENE-TYPE REACTIONS - A DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (+)-A-ALLOKAINIC ACID
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ROBBIANI, C
BATTIG, K
HELVETICA CHIMICA ACTA, 1980, 63 (07) : 2015 - 2018
[9] Novel synthesis of αa-amino acid derivatives through catalytic, enantioselective ene reactions of α-imino esters
Drury, William J. III
Ferraris, Dana
Cox, Christopher
Young, Brandon
Lectka, Thomas
Journal of the American Chemical Society, 1998, 120 (42):
[10] Catalytic hetero-ene reactions of 5-methyleneoxazolines: highly enantioselective synthesis of 2,5-disubstituted oxazole derivatives
Luo, Weiwei
Zhao, Jiannan
Yin, Chengkai
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
CHEMICAL COMMUNICATIONS, 2014, 50 (56) : 7524 - 7526

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