Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols

被引：5

作者：

Tsygankov, Alexey A. ^{[1
]}

Chun, Man-Seog ^{[2
]}

Samoylova, Alexandra D. ^{[1
]}

Kwon, Seongyeon ^{[2
]}

Kreschenova, Yuliya M. ^{[1
]}

Kim, Suhyeon ^{[2
]}

Shin, Euijin ^{[2
]}

Oh, Jinho ^{[2
]}

Strelkova, Tatyana V. ^{[3
]}

Kolesov, Valerii S. ^{[3
]}

Zubkov, Fedor I. ^{[4
]}

Semenov, Sergei E. ^{[1
]}

Fedyanin, Ivan V. ^{[3
]}

Chusov, Denis ^{[1
,3
,4
]}

机构：

[1] Moscow Chem Lyceum, Tamozhenniy Proezd 4, Moscow, Russia

[2] Korea Adv Inst Sci & Technol, Korea Sci Acad, 105-47 Baegyanggwanmun Ro, Busan 47162, South Korea

[3] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilova Str 28, Moscow 119991, Russia

[4] Peoples Friendship Univ Russia, Dept Organ Chem, 6 Miklukho Maklaya St, Moscow 117198, Russia

来源：

SYNLETT | 2017年 / 28卷 / 05期

基金：

俄罗斯科学基金会;

关键词：

aldol reaction; organocatalysis; asymmetric catalysis; hydroxy acids; diamines; Meervein-Ponndorf-Verley reaction; Henry reaction; MUKAIYAMA ALDOL REACTION; ALPHA-KETO ESTERS; AMINE-IMINE CATALYST; AQUEOUS-MEDIUM; CARBON CENTER; CONSTRUCTION; WATER; PROLINEAMIDE; PROLINAMIDE; ALDEHYDES;

D O I：

10.1055/s-0036-1588382

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of N,N'-dialkylated derivatives of (1R, 2R)-cyclohexane-1,2-diamine were synthesized, and a new approach to the one-pot preparation of this type of amine was demonstrated. The prepared diamines were used as organocatalysts for the two-step synthesis of ahydroxy gamma-keto esters from arenes, chlorooxoacetates, and ketones; they were also used as chiral ligands for Meervein-Ponndorf-Verley reductions and Henry reactions.

引用

页码：615 / 619

页数：5

共 50 条

[31] Synthesis of N,N′-disubstituted cyclic 1,2-diamines derived from (1R,2R)-1,2-diaminocyclohexane
Boyd, E
Coumbarides, GS
Eames, J
Jones, RVH
Motevalli, M
Stenson, RA
Suggate, MJ
TETRAHEDRON LETTERS, 2005, 46 (20) : 3473 - 3478
[32] Synthesis and derivatisation of N,N′-trisubstituted 1,2-diamines derived from (1R,2R)-1,2-diaminocyclohexane
Boyd, E
Coumbarides, GS
Eames, J
Jones, RVH
Stenson, RA
Suggate, MJ
TETRAHEDRON LETTERS, 2005, 46 (20) : 3479 - 3484
[33] Asymmetric Synthesis of 1,2-Diamines bearing Tetrasubstituted Centers from Nonstabilized Azomethine Ylides and N-Sulfinylketimines under Bronsted Acid Catalysis
Izquierdo, Cristina
Esteban, Francisco
Garcia Ruano, Jose Luis
Fraile, Alberto
Aleman, Jose
ORGANIC LETTERS, 2016, 18 (01) : 92 - 95
[34] ASYMMETRIC-SYNTHESIS .18. PREPARATION OF CHIRAL 1,2-DIAMINES VIA THE CN(R,S) METHOD - APPLICATION TO THE SYNTHESIS OF AN ANALOG OF TETRAPONERINE
ZHU, JP
QUIRION, JC
HUSSON, HP
TETRAHEDRON LETTERS, 1989, 30 (38) : 5137 - 5140
[35] Asymmetric Synthesis of Axially Chiral N, N-1,2-Pentatomic Heterobiaryl Diamines by an Organocatalytic Arylation Reaction
Zhao, Shi-Na
Li, Qian
Qiao, Xiu-Xiu
He, Yonghui
Li, Ganpeng
Zhao, Xiao-Jing
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (70)
[36] N-Alkylation-coupling reaction of imines promoted by alkylaluminum reagents, leading to a facile synthesis of 1,2-diamines
Shimizu, M
Niwa, Y
TETRAHEDRON LETTERS, 2001, 42 (15) : 2829 - 2832
[37] SYNTHESIS OF CHELATING AGENS RELATED TO CYCLOHEXANE-1,2-DIAMINE-NNN'N'-TETRA-ACETIC ACID
BELCHER, R
HOYLE, W
WEST, TS
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (FEB): : 667 - &
[38] REACTION OF GROUP-4 ORGANOMETALLIC COMPOUNDS .32. MODIFIED SYNTHESIS OF IMIDAZOLIDINES WITH N,N'-BIS(TRIMETHYLSILYL)-1,2-DIAMINES
SUZUKI, H
OHASHI, M
ITOH, K
MATSUDA, I
ISHII, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (06) : 1922 - 1924
[39] Synthesis of New Chiral Secondary 1,2-Diamines Based on Levopimaric Acid and Their Use as Ligands in Copper(II)-Catalyzed Asymmetric Henry Reaction
V. N. Konev
Z. P. Pai
T. B. Khlebnikova
Russian Journal of Organic Chemistry, 2020, 56 : 604 - 612
[40] Synthesis of New Chiral Secondary 1,2-Diamines Based on Levopimaric Acid and Their Use as Ligands in Copper(II)-Catalyzed Asymmetric Henry Reaction
Konev, V. N.
Pai, Z. P.
Khlebnikova, T. B.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (04) : 604 - 612

← 1 2 3 4 5 →