Highly selective and high-yielding rotaxane synthesis via aminolysis of prerotaxanes consisting of a ring component and a stopper unit

被引：37

作者：

Hirose, Keiji ^{[1
]}

Nishihara, Keiji ^{[1
]}

Harada, Naoki ^{[1
]}

Nakamura, Yamato ^{[1
]}

Masuda, Daisuke ^{[1
]}

Araki, Masami ^{[1
]}

Tobe, Yoshito ^{[1
]}

机构：

[1] Osaka Univ, Div Frontier Mat Sci, Grad Sch Engn Sci, Toyonaka, Osaka 5638531, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 16期

关键词：

D O I：

10.1021/ol070999w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly rotaxane-selective synthesis via aminolysis of prerotaxanes, which were composed of a phenolic pseudo-crown ether as a ring component and a bulky stopper unit, was developed. The best result was obtained in the case of aminolysis of 3b with 3,5-dimethylbenzylamine which proceeded quantitatively with ca. 100% rotaxane selectivity forming the corresponding rotaxane 5b. The rotaxanes were formed by kinetically controlled attack of the amine from the backside of the ring component of the prerotaxanes.

引用

页码：2969 / 2972

页数：4

共 2 条

[1] One-Pot High-Yielding Synthesis of the DPP4-Selective Inhibitor ABT-341 by a Four-Component Coupling Mediated by a Diphenylprolinol Silyl Ether
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (12) : 2824 - 2827
[2] Toward high-yielding supramolecular synthesis:: Directed assembly of ditopic imidazoles/benzimidazoles and dicarboxylic acids into cocrystals via selective O-H•••N hydrogen bonds
Aakeröy, CB
Desper, J
Leonard, B
Urbina, JF
CRYSTAL GROWTH & DESIGN, 2005, 5 (03) : 865 - 873

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