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Ethylaluminium Dichloride Induced Reactions of Acetals with Unsaturated Carboxylic Esters: Synthesis of Homoallyl Ethers

✍ Scribed by Metzger, Jürgen O. ;Biermann, Ursula

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 409 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619961119

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✦ Synopsis

Abstract

The ethylaluminium dichloride induced reactions of methyl 10‐undecenoate (1) with dimethyl acetals of formaldehyde 2a, acetaldehyde 2b, isobutyraldehyde 2c, and pivaldehyde 2d gave the corresponding homoallyl ethers 3a, 3b, 3c, and 3d in yields of 48–70%. The products were obtained as mixtures of the (E) and (Z) stereoisomers. With formaldehyde dimethyl acetal (2a), methyl oleate (6), and methyl petroselinate (11) gave the corresponding regioisomeric (E)‐configured homoallyl ethers 7/8 and 12/13.

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