Catalytic diastereo- and positionselective oxidative mono-cyclization of 1,5,9-trienes and polyenes

被引：28

作者：

Goehler, Sabrina ^{[1
]}

Stark, Christian B. W. ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 10期

关键词：

D O I：

10.1039/b702877f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium tetroxide (1 mol%) has been used as a catalyst for the oxidative mono-cyclization of 1,5,9-trienes and polyenes. The poly-unsaturated substrates underwent mono-cyclization with a high degree of diastereo- and positionselectivity to produce mono-tetrahydrofuran diols with a varying degree of unsaturation. Up to four new stereogenic centers were created in this single step transformation. The remarkable positionselectivity appears to be a result of relative electronic properties of the double bonds within the polyolefinic substrates in conjunction with conformational constraints.

引用

页码：1605 / 1614

页数：10

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