Highly stereoselective allylic ethylation with alkoxytitanacyclopropane reagents. Synthesis of (1 R/ S,7 R)-1,7-dimethylnonyl propanoate, the Western corn rootworm sex attractant

Allylic ethylation of 2-(( E)-dodec-2-en-4-yloxy)tetrahydro-2 H-pyran with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide proceeds via a S N2′ pathway to afford ( E)-3-methyltridec-4-ene with excellent syn-diastereoselecivity. This transformation is used as a key step in the syn...

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Bibliographic Details
Published in:Tetrahedron letters 2008-12, Vol.49 (49), p.6959-6961
Main Authors: Isakov, Vladimir E., Kulinkovich, Oleg G.
Format: Article
Language:English
Subjects:
Alkoxytitanacyclopropane reagents
Allylic ethers
Allylic ethylation
Diabrotica virgifera virgifera
Diastereoselectivity
Pheromones
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Summary:Allylic ethylation of 2-(( E)-dodec-2-en-4-yloxy)tetrahydro-2 H-pyran with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide proceeds via a S N2′ pathway to afford ( E)-3-methyltridec-4-ene with excellent syn-diastereoselecivity. This transformation is used as a key step in the synthesis of (1 R/S,7 R)-1,7-dimethylnonyl propanoate, the Western corn rootworm ( Diabrotica virgifera virgifera) sex attractant.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.08.063