Stereospecific, R2AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism

DOI: 10.1002/hlca.19840670312

Source and publish data:

Helvetica Chimica Acta p. 730 - 738 (1984)

Update date:2022-09-26

Topics: Stereospecific Concerted Mechanism

Authors:

Oppolzer, Wolfgang

Mirza, Sohail

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Article abstract of DOI:10.1002/hlca.19840670312

Treatment of the 83percent-trans-13CH3-labelled 1,6-dienoate 7 with Et2AlCl at -78 deg C provided in high yield the ene product 9 containing 83percent 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).

Full text of DOI:10.1002/hlca.19840670312

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