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Ethylaluminium Dichloride Induced Reactions of Acetals with Unsaturated Carboxylic Esters: Synthesis of Homoallyl Ethers
Author(s) -
Metzger Jürgen O.,
Biermann Ursula
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961119
Subject(s) - chemistry , isobutyraldehyde , acetaldehyde , acetal , formaldehyde , organic chemistry , medicinal chemistry , catalysis , ethanol
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 .