Diastereoselective Diels-Alder Reactions of 1,7,9-Decatrien-3-ones to Highly Substituted Octalin Derivatives

被引：1

作者：

Thiemermann , Jutta ^{[1
]}

Schnaubelt, Jurgen ^{[1
]}

Zimmer, Reinhold ^{[2
]}

Reissig, Hans-Ulrich ^{[2
]}

机构：

[1] Tech Univ Dresden, Fachrichtung Chem & Lebensmittelchem, D-01062 Dresden, Germany

[2] Free Univ Berlin, Inst Chem & Biochem, Takustr 3, D-14195 Berlin, Germany

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 24期

关键词：

Diels-Alder reaction; intramolecular cycloaddition; Lewis acid; diastereoselectivity; titanium; CHELATE-CONTROLLED ADDITIONS; TITANIUM(IV) COMPLEXES; ENDO/EXO-SELECTIVITY; CRYSTAL-STRUCTURE; METHYL; KEY; STEREOSELECTIVITY; STEREOCONTROL; ORIGIN; ROUTE;

D O I：

10.1055/s-0036-1588323

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on an efficient synthesis of 1,7,9-decatrien-3-one precursors we studied their thermal and Lewis acid-promoted intramolecular Diels-Alder reactions to octalin derivatives. Whereas the thermal cycloadditions showed only cis/trans selectivities close to 35: 65, the transformations were strongly influenced by the type of Lewis acid employed. With mono-coordinating Lewis acids such as BF3, cis/trans ratios of up to 85: 15 were observed, whereas di-coordinating Lewis acids such as TiCl2(OiPr)(2) induce fairly high trans-selectivity. This remarkable switch of diastereoselectivity is discussed.

引用

页码：4533 / 4540

页数：8

共 68 条

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