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Chiral (E,E)-1,4-dialkoxy-1,3-butadienes. 1. Stereoselective synthesis

✍ Scribed by Marina Virgili; Albert Moyano; Miquel A. Pericàs; Antoni Riera

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 209 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01622-5

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✦ Synopsis

A two step, totally stereoselective synthesis of (E,E)-lA-dialkoxy-l,3-butadienes from chiral secondary alcohols has been developed. The key step involves the regio-and stereoselective hydrozirconation of alkoxyethynes derived from chiral alcohols; the intermediate (E)-(2alkoxyvinyl)zircouium compounds, after treatment with cuprous chloride and thermally induced decomposition of the corresponding (2-alkoxyvinyl)copper, give the dialkoxybutadienes in moderate yield but with complete (E,E)diastercoselectivity.

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