Organocatalytic Asymmetric Domino Aza-Michael-Mannich Reaction: Synthesis of Tetrahydroimidazopyrimidine Derivatives

被引：33

作者：

Li, Hong ^{[1
]}

Zhao, Junling ^{[1
]}

Zeng, Lili ^{[1
]}

Hu, Wenhui ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Guangzhou 510530, Guangdong, Peoples R China

[2] State Key Lab Resp Dis, Guangzhou 510120, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 19期

关键词：

DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; ORGANIC CATALYSIS; TETRAHYDRO-1,2-OXAZINES; AMINOCATALYSIS; STEREOCENTERS; HETEROCYCLES; ALKYLATION;

D O I：

10.1021/jo201301p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly substituted tetrahydroimidazopyrimidine derivatives with three chiral centers have been synthesized for the first time using an organocatalytic asymmetric domino aza-Michael Mannich reaction of alpha,beta-unsaturated aldehydes and N-arylidene-1H-imidazol-2-amines. This efficient approach furnishes the products in good yields (42-87%) with excellent stereoselectivities (>20:1 dr, up to >99% ee).

引用

页码：8064 / 8069

页数：6

共 50 条

[1] Asymmetric Synthesis of Polyfunctionalized Pyrrolidines via a Thiourea Catalyzed Domino Mannich/Aza-Michael Reaction
Enders, Dieter
Goeddertz, Dominik P.
Beceno, Christian
Raabe, Gerhard
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 2863 - 2868
[2] Organocatalytic Asymmetric Synthesis of Tetracyclic Pyridocarbazole Derivatives by Using a Diels-Alder/aza-Michael/Aldol Condensation Domino Reaction
Enders, Dieter
Joie, Celine
Deckers, Kristina
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) : 10818 - 10821
[3] Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction
Mukhopadhyay, Soumendranath
Pan, Subhas Chandra
CHEMICAL COMMUNICATIONS, 2018, 54 (08) : 964 - 967
[4] Asymmetric Synthesis of Dihydrofurans via Organocatalytic Domino Michael-Alkylation Reaction
Feng, Juhua
Lin, Lili
Yu, Kunru
Liu, Xiaohua
Feng, Xiaoming
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1305 - 1310
[5] Organocatalytic Domino Mannich Aza-Michael Reactions towards the Stereoselective Synthesis of Highly Substituted Pipecolic Esters
Khaliel, Souad
Nandakumar, Mecheril Valsan
Krautscheid, Harald
Schneider, Christoph
SYNLETT, 2008, (17) : 2705 - 2707
[6] Asymmetric Organocatalytic Aza-Michael Reactions of Isatin Derivatives
Zari, Sergei
Metsala, Andrus
Kudrjashova, Marina
Kaabel, Sandra
Jaerving, Ivar
Kanger, Tonis
SYNTHESIS-STUTTGART, 2015, 47 (06): : 875 - 886
[7] Mechanochemically Activated Asymmetric Organocatalytic Domino Mannich Reaction-Fluorination
Kristofikova, Dominika
Meciarova, Maria
Rakovsky, Erik
Sebesta, Radovan
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (38) : 14417 - 14424
[8] Asymmetric Synthesis of Tetrahydropyridines via an Organocatalytic One-Pot Multicomponent Michael/Aza-Henry/Cyclization Triple Domino Reaction
Bluemel, Marcus
Chauhan, Pankaj
Hahn, Robert
Raabe, Gerhard
Enders, Dieter
ORGANIC LETTERS, 2014, 16 (22) : 6012 - 6015
[9] Organocatalytic asymmetric Mannich reaction
Ma Jingjun
Li Ning
Wu Qiuhua
Zhou Xin
Zang Xiaohuan
Wang Chun
PROGRESS IN CHEMISTRY, 2008, 20 (01) : 76 - 86
[10] Asymmetric synthesis of polysubstituted chiral chromans via an organocatalytic oxa-Michael-nitro-Michael domino reaction
Tang, Cheng-Ke
Feng, Kai-Xiang
Xia, Ai-Bao
Li, Chen
Zheng, Ya-Yun
Xu, Zhen-Yuan
Xu, Dan-Qian
RSC ADVANCES, 2018, 8 (06): : 3095 - 3098

← 1 2 3 4 5 →