Practical asymmetric synthesis of 1,2-diamines in the 3-aminoazepane series

被引：23

作者：

Cutri, S

Bonin, M

Micouin, L

Husson, HP

Chiaroni, A

机构：

[1] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France

[2] Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 07期

关键词：

D O I：

10.1021/jo026711s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and versatile method for the enantio- and diastereoselective synthesis of mono- or disubstituted 3-aminoazepanes is described. The key step involves a highly regio- and diastereoselective tandem ring-enlargement/alkylation or reduction process. This novel synthetic route provides enantiomerically pure constrained diamines interesting as scaffolds for medicinal chemistry.

引用

页码：2645 / 2651

页数：7

共 50 条

[31] Synthesis of 1,2-Diamines from Vinyl Sulfonium Salts and Arylamines
Wang, Cheng
Liu, Biao
Shao, Zeyu
Zhou, Junqi
Shao, Andong
Zou, Liang-Hua
Wen, Jian
ORGANIC LETTERS, 2022, 24 (35) : 6455 - 6459
[32] Preparation of polymer-supported chiral 1,2-diamines and their application to asymmetric reaction
Itsuno, S
Haraguchi, N
Takahashi, M
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2005, 63 (12) : 1253 - 1263
[33] CONVERSION OF ALKENES TO 1,2-DIAZIDES AND 1,2-DIAMINES
FRISTAD, WE
BRANDVOLD, TA
PETERSON, JR
THOMPSON, SR
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19): : 3647 - 3649
[34] Kinetic Resolution of 1,2-Diamines via Organocatalyzed Asymmetric Electrophilic Aminations of Anilines
Xie, Jinglei
Guo, Zheng
Liu, Wei
Zhang, Dekun
He, Yu-Peng
Yang, Xiaoyu
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (14) : 1674 - 1680
[35] Green asymmetric synthesis of Warfarin and Coumachlor in pure water catalyzed by quinoline-derived 1,2-diamines
Kucherenko, Alexander S.
Kostenko, Alexey A.
Zhdankina, Galina M.
Kuznetsova, Olga Yu.
Zlotin, Sergei G.
GREEN CHEMISTRY, 2018, 20 (03) : 754 - 759
[36] An efficient synthesis of tetrasubstituted cyclohexyl-1,2-diamines
Arjan, H
Boyd, E
Coumbarides, GS
Eames, J
Jones, RVH
Stenson, RA
Suggate, MJ
TETRAHEDRON LETTERS, 2005, 46 (11) : 1921 - 1925
[37] Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades
Ford, Grayson J.
Kress, Nico
Mattey, Ashley P.
Hepworth, Lorna J.
Baldwin, Christopher R.
Marshall, James R.
Seibt, Lisa S.
Huang, Min
Birmingham, William R.
Turner, Nicholas J.
Flitsch, Sabine L.
CHEMICAL COMMUNICATIONS, 2020, 56 (57) : 7949 - 7952
[38] Synthesis and characterization of novel chiral 1,2-diamines derived from α-pinene
Suzuki, T
Shibata, A
Morohashi, N
Ohba, Y
CHEMISTRY LETTERS, 2005, 34 (11) : 1476 - 1477
[39] An aldimine cross-coupling for the diastereoselective synthesis of unsymmetrical 1,2-diamines
Kison, C
Meyer, N
Opatz, T
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (35) : 5662 - 5664
[40] Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines
Lyu, Jiyuan
Claraz, Aurelie
Vitale, Maxime R.
Allain, Clemence
Masson, Geraldine
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (20): : 12843 - 12855

← 1 2 3 4 5 →