From cyclooctatetraene to chiral polyfunctionalized C8 building blocks-meso-persubstituted oxepanes and azepanes

被引：16

作者：

Armbruster, J ^{[1
]}

Stelzer, F ^{[1
]}

Landenberger, P ^{[1
]}

Wieber, C ^{[1
]}

Hunkler, D ^{[1
]}

Keller, M ^{[1
]}

Prinzbach, H ^{[1
]}

机构：

[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 29期

关键词：

cyclooctatetraene-oxides; 7-heterobicyclo[4.2.1]nonenes; 7,8-diazabicyclo[4.2.2]decenes; azepanes; oxepanes;

D O I：

10.1016/S0040-4039(00)00905-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclooctatetraene-via its 1 alpha,2 alpha,5 alpha,6 alpha-diepoxy-3 beta,4 beta-diol (4)-is the basis for the construction of specifically polyfunctionalized C-8 building blocks. Whilst with monofunctional nucleophiles only monosubstitution and with I,1-dinucleophiles neatly intramolecular cyclization to aza(oxa,thia)bicyclo[4.2.1]nonenes occurred, the desired substitution pattern became, in principle, accessible with 1,2-disubstituted hydrazines. The usefulness of the 7-hetero[4.2.1]bicycles for the preparation of meso-persubstituted azepanes and oxepanes is exemplified. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5483 / 5487

页数：5

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