Practical asymmetric henry reaction catalyzed by a chiral Diamine-Cu(OAc)2 complex

被引：180

作者：

Arai, Takayoshi ^{[1
]}

Watanabe, Masahiko ^{[1
]}

Yanagisawa, Akira ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage 2638522, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 18期

关键词：

D O I：

10.1021/ol7014362

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral diamine ligand 3 was designed and synthesized from (R,R)-1,2-diphenylethylenediamine, (S)-2,2'-dibromomethyl-1,1'-binaphthalene, and o-xylylene dibromide. The resulting 3-Cu(OAc)(2) complex was a highly efficient catalyst for the Henry reaction, giving the various nitroaldols with over 90% ee (up to > 99%). The reaction was performed in n-propyl alcohol at room temperature, and the Henry adducts were produced in high yield with excellent enantiomeric excess; these attributes are desirable in a catalyst for practical use.

引用

页码：3595 / 3597

页数：3

共 50 条

[41] A Highly anti-Selective Asymmetric Henry Reaction Catalyzed by a Chiral Copper Complex: Applications to the Syntheses of (+)-Spisulosine and a Pyrroloisoquinoline Derivative
Xu, Kun
Lai, Guoyin
Zha, Zhenggen
Pan, Susu
Chen, Huanwen
Wang, Zhiyong
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (39) : 12357 - 12362
[42] Cu(OAc)2 catalyzed Sonogashira cross-coupling reaction in amines
Sheng Mei Guo Chen Liang Deng Jin Heng Li~* Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research(Ministry of Education)
Chinese Chemical Letters, 2007, (01) : 13 - 16
[43] Recyclable chiral Cu(II) macrocyclic salen complex catalyzed enantioselective aza-Henry reaction of isatin derived N-Boc ketimines and its application for the synthesis of β-diamine
Menapara, Tusharkumar
Choudhary, Manoj K.
Tak, Rajkumar
Kureshy, Rukhsana I.
Khan, Noor-ul H.
Abdi, Sayed H. R.
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 421 : 161 - 166
[44] Cu(OAc)2 catalyzed Sonogashira cross-coupling reaction in amines
Guo, Sheng Mei
Deng, Chen Liang
Li, Jin Heng
CHINESE CHEMICAL LETTERS, 2007, 18 (01) : 13 - 16
[45] Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction
Mao, Pu
Yang, Liangru
Xiao, Yongmei
Yuan, Jinwei
Mai, Wenpeng
Gao, Jie
Zhang, Xinchi
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (02) : 443 - 448
[46] Chiral 1,1′-binaphthylazepine derived amino alcohol catalyzed asymmetric Henry reaction
Guo, Zong-Liang
Zhong, Shi
Li, Yong-Bo
Lu, Gui
TETRAHEDRON-ASYMMETRY, 2011, 22 (02) : 238 - 245
[47] Asymmetric domino Michael-Henry reaction of 1,2-diones with nitroolefins catalyzed by a chiral bisoxazolidine-Ni(acac)2 complex
Liang, Qian
He, Junpeng
Ni, Bukuo
TETRAHEDRON-ASYMMETRY, 2014, 25 (15) : 1146 - 1149
[48] ASYMMETRIC [2 + 2] CYCLOADDITION REACTION CATALYZED BY A CHIRAL TITANIUM REAGENT
NARASAKA, K
HAYASHI, Y
SHIMADZU, H
NIIHATA, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) : 8869 - 8885
[49] Asymmetric [2 + 2] cycloaddition reaction catalyzed by a chiral titanium reagent
1600, (114):
[50] Asymmetric reductive Mannich reaction to ketimines catalyzed by a Cu(I) complex
Graduate School of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Journal of the American Chemical Society, 2008, 130 (48): : 16146 - 16147

← 1 2 3 4 5 →