Journal of Organic Chemistry p. 3685 - 3689 (1983)
Update date:2022-07-30
Topics:
Snider, Barry B.
Phillips, Gary B.
Trimethyl 2-phosphonoacrylate (1a) undergoes EtAlCl2-catalyzed ene reactions in high yield at 0 deg C with most classes of alkenes.The products are useful reagents for the phosphonate modification of the Wittig reaction.EtAlCl2-catalyzed ene reaction of 1a with 6-methyl-5-hepten-2-one (18) at -78 deg C gives 19, which undergoes an intramolecular Wittig reaction to give 21.Ethyl α-methylene-1-cyclohexenebutanoate (16) undergoes a Lewis acid initiated cyclization to give the cyclopropane 30 and octalins 31 and 32.
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Doi:10.1021/ol901542n
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