Stereoselective Synthesis of 2Z,4E-Configured Dienoates through Tethered Ring Closing Metathesis

被引：9

作者：

Schmidt, Bernd ^{[1
]}

Audoersch, Stephan ^{[1
]}

Kunz, Oliver ^{[1
]}

机构：

[1] Univ Potsdam, Inst Chem, Karl Liebknecht Str 24-25, D-14476 Potsdam, Germany

来源：

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

关键词：

allyl alcohols; dienes; ring closing metathesis; ruthenium; elimination; OLEFIN CROSS-METATHESIS; STEREOCONTROLLED SYNTHESIS; BIOLOGICAL-ACTIVITY; ESTER HOMOLOGATION; CARBOXYLIC-ACIDS; NATURAL-PRODUCTS; ANALOGS; REARRANGEMENT; DERIVATIVES; FUNGUS;

D O I：

10.1055/s-0035-1562536

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step sequence leading from racemic allylic alcohols and vinylacetic acid to ethyl (2Z,4E)-dienoatesis described. The sequence involves Steglich esterification of the reactants, followed by a one-pot ring closing metathesis-base induced elimination-alkylation reaction to furnish the products in high stereoselectivity. Trapping of the intermediate sodium carboxylates is accomplished efficiently using Meerwein's salt Et3OBF4.

引用

页码：4509 / 4518

页数：10

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