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Publication 99
- Stereospecific, R2AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism
Oppolzer, W.; Mirza, S.
Helv. Chim. Acta 1984, 67, 730-738
Treatment of the 83%-trans-13CH3-labelled 1,6-dienoate 7 with Et2AlCl at–78° provided in high yield the ene product 9 containing 83% 13C localized in the olefinic C(8)-methylene group. Accordingly, H-transfer occurs exclusively from the trans-methyl group of 7, consistent with a concerted ene process 7 9 thereby ruling out an intermediate cation 8 (Scheme 4).
DOI : 10.1002/hlca.19840670312