Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane

Gregory K Friestad; Hye Jin Lee

doi:10.1021/ol901613k

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Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane

Journal article

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Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane

Gregory K Friestad and Hye Jin Lee

Organic letters, Vol.11(17), pp.3958-3961

09/03/2009

DOI: 10.1021/ol901613k

PMID: 19663466

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Abstract

Addition of allyltributylstannane to 2,7-dioxabicyclo[2.2.1]heptane in the presence of TiCl(4) produces 5-allyl-2-(hydroxymethyl)tetrahydrofuran with a trans/cis ratio of 93:7. The trans-selectivity is also observed in additions of various other carbon nucleophiles.

Heptanes - chemistry

Bridged Bicyclo Compounds - chemistry

Combinatorial Chemistry Techniques

Furans - chemistry

Stereoisomerism

Molecular Structure

Catalysis

Furans - chemical synthesis

Tin Compounds - chemistry

Details

Title: Subtitle: Trans-2,5-disubstituted tetrahydrofurans via addition of carbon nucleophiles to the strained bicyclic acetal 2,7-dioxabicyclo[2.2.1]heptane
Creators: Gregory K Friestad - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA. gregory-friestad@uiowa.edu
Hye Jin Lee
Resource Type: Journal article
Publication Details: Organic letters, Vol.11(17), pp.3958-3961
Publisher: United States
DOI: 10.1021/ol901613k
PMID: 19663466
ISSN: 1523-7060
eISSN: 1523-7052
Language: English
Date published: 09/03/2009
Academic Unit: Chemistry
Record Identifier: 9983985963902771

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