Selective synthesis of chiral dioxabicyclo[4.4.0]decane and dioxabicyclo[5.3.0]decane from 3,4-bisallyloxy-but-1-yne derivatives via ruthenium-catalyzed en-yn-ene metathesis

Chang-Jung Wu; Reniguntala J Madhushaw; Rai-Shung Liu

doi:10.1021/jo0301548

Selective synthesis of chiral dioxabicyclo[4.4.0]decane and dioxabicyclo[5.3.0]decane from 3,4-bisallyloxy-but-1-yne derivatives via ruthenium-catalyzed en-yn-ene metathesis

J Org Chem. 2003 Oct 3;68(20):7889-92. doi: 10.1021/jo0301548.

Authors

Chang-Jung Wu¹, Reniguntala J Madhushaw, Rai-Shung Liu

Affiliation

¹ Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, 30043, ROC.

PMID: 14510573
DOI: 10.1021/jo0301548

Abstract

We prepared a series of chiral 3,4-bisallyloxy-but-1-ynes having syn and anti configurations. Treatment of these substrates with Grubbs catalyst Cl2(PCy3)2Ru=CHPh (3 mol %) preferably gave chiral dioxabicyclo[4.4.0]decane (yields > 55%) in addition to dioxabicyclo[5.3.0]decane in minor proportions. On substitution of the 4-allyloxy group of these substrates with a 4-but-2-enyloxy group, the metathesis reactions produced only dioxabicyclo[5.3.0]decane in the presence of Grubbs ruthenium-imidazolidene carbene catalyst.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkanes / chemical synthesis*
Alkanes / chemistry
Alkynes / chemistry*
Allyl Compounds / chemistry
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Magnetic Resonance Spectroscopy
Ruthenium / chemistry
Stereoisomerism

Substances

Alkanes
Alkynes
Allyl Compounds
Bridged Bicyclo Compounds, Heterocyclic
Ruthenium
decane