Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes

被引：65

作者：

Jinks, Michael A. ^{[1
]}

de Juan, Alberto ^{[1
]}

Denis, Mathieu ^{[1
]}

Fletcher, Catherine J. ^{[1
]}

Galli, Marzia ^{[1
]}

Jamieson, Ellen M. G. ^{[1
]}

Modicom, Florian ^{[1
]}

Zhang, Zhihui ^{[1
]}

Goldup, Stephen M. ^{[1
]}

机构：

[1] Univ Southampton, Chem, Southampton SO17 1BJ, Hants, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 45期

基金：

英国工程与自然科学研究理事会; 欧洲研究理事会;

关键词：

chirality; CuAAC; rotaxane; stereoselective synthesis; supramolecular chemistry; AZIDE-ALKYNE CYCLOADDITION; ACTIVE-TEMPLATE SYNTHESIS; EFFICIENT DIAZO-TRANSFER; INTERLOCKED MOLECULES; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC CATALYSIS; ALPHA-CYCLODEXTRIN; SOLOMON LINK; CATENANES; MACROCYCLES;

D O I：

10.1002/anie.201808990

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98:2 d.r. using a readily available alpha-amino acid-derived azide. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.

引用

页码：14806 / 14810

页数：5

共 50 条

[41] Stereoselective synthesis of azasugars from chiral aziridine
Eum, Heesung
Lee, Won Koo
Ha, Hyun-Joon
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[42] STEREOSELECTIVE SYNTHESIS OF THE CHIRAL SEQUENCE OF ERYTHRONOLIDE-A
STORK, G
PATERSON, I
LEE, FKC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) : 4686 - 4688
[43] Stereoselective synthesis of topologically chiral molecular entanglements
Lewis, James E. M.
CHEM, 2023, 9 (04): : 762 - 764
[44] Stereoselective Synthesis via Chiral Pinanone Imine
MI AiQiao
CHEN YuanWei
XIAO Xun
LIU ShiKui
WU LanJun
JIANG YaoZhong Chengdu Institute of Organic Chemistry Academia Sinica Chengdu
有机化学, 1993, (02) : 199 - 201
[45] CARBOHYDRATES AS CARRIER OF CHIRAL INFORMATION IN STEREOSELECTIVE SYNTHESIS
KUNZ, H
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 68 - CARB
[46] Stereoselective synthesis and molecular modeling of chiral cyclopentanes
Abdel-Jalil, Raid J.
Steinbrecher, Thomas
Al-Harthy, Thuraya
Mahal, Ahmed
Abou-Zied, Osama K.
Voelter, Wolfgang
CARBOHYDRATE RESEARCH, 2015, 415 : 12 - 16
[47] Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds
Wojaczynska, Elzbieta
Wojaczynski, Jacek
CHEMICAL REVIEWS, 2020, 120 (10) : 4578 - 4611
[48] Stereoselective Synthesis of a Topologically Chiral Solomon Link
Cui, Zheng
Lu, Ye
Gao, Xiang
Feng, Hui-Jun
Jin, Guo-Xin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (32) : 13667 - 13671
[49] Towards the stereoselective synthesis of inherently chiral pseudorotaxanes
Mobian, P
Banerji, N
Bernardinelli, G
Lacour, J
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (02) : 224 - 231
[50] CHIRAL AZIRIDINES - THEIR SYNTHESIS AND USE IN STEREOSELECTIVE TRANSFORMATIONS
TANNER, D
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (06): : 599 - 619

← 1 2 3 4 5 →