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A single example of the catalytic addition of 1-octene to a β-unsubstituted enone was previously reported by Jamison and co-workers (reference[5]). The reaction afforded enol silanes with the 1,1- and 1,2-disubstitution pattern as a 4:1 mixture of regioisomers 4 and 2. Aromatic alkynes cleanly provided the 1,2-disubstituted isomer 2. As this procedure was largely developed for ethylene additions to generate product 3, the generality with alkyl-substituted olefins for obtaining the 1,1-disubstitution pattern (4) across a range of substrates was not established in this report. The report from Ogoshi et al. (reference[6]) illustrated that, without silyl triflate promoters and using β-substituted enones, the 1,2-disubstituted isomer 2 was exclusively obtained, irrespective of the electronic nature of the alkene.
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78149448580
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Jamison has extensively developed the synthesis of 1,1-disubstituted alkenes by catalytic alkene additions to aldehydes
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