One-pot synthesis of macrocyclic compounds possessing two cyclobutane rings by sequential inter- and intramolecular [2+2] photocycloaddition reactions

被引：16

作者：

Miyauchi, Hideki ^{[1
]}

Ikematsu, Chie ^{[1
]}

Shimazaki, Toshiaki ^{[2
]}

Kato, Shinichiro ^{[2
]}

Shinmyozu, Teruo ^{[2
]}

Shimo, Tetsuro ^{[1
]}

Somekawa, Kenichi ^{[1
]}

机构：

[1] Kagoshima Univ, Fac Engn, Dept Chem Engn & Appl Chem, Kagoshima 8900065, Japan

[2] Kyushu Univ, Inst Mat Chem & Engn, Fukuoka 8128581, Japan

来源：

TETRAHEDRON | 2008年 / 64卷 / 18期

关键词：

photocycloaddition reactions; di-2-pyrones; diolefins; macrocyclic compounds;

D O I：

10.1016/j.tet.2008.02.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sensitized photocycloaddition reactions of 6,6'-dimethyl-4,4-[1,3-bis(methylenoxy)phenylene]-di-2-pyrone (1) with electron-poor alpha,omega-diolefins such as ethylene diacrylate (2a) and polyoxyethylene dimethacrylates (2b-d) afforded site- and stereoselective macrocyclic dioxatetralactones (3a-d) and (4b) having 18- to 25-membered rings across the C5-C6 and C5'-C6' double bonds, or C5-C6 and C3'-C4' double bonds in 1, respectively. Similar photoreactions of I with electron-rich alpha,omega-diolefins such as poly(ethylene glycol)divinyl ether (2e and 2f) afforded crown ether-type macrocyclic compounds (5e and 5f) having 18- and 21-membered rings across the C3-C4 and C3'-C4' double bonds in 1, respectively. The stereochemical features of 3b, 5e-xx, and 5e-nn were determined by the X-ray crystal analysis. The reaction mechanism was inferred by MO methods. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4108 / 4116

页数：9

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