2015
DOI: 10.1039/c5sc01553g
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Rh-catalyzed desymmetrization of α-quaternary centers by isomerization-hydroacylation

Abstract: A Rh-catalyzed desymmetrization of α,α-bis(allyl)aldehydes occurs by enantioselective isomerization followed by olefin-directed hydroacylation.

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Cited by 56 publications
(34 citation statements)
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“…Next, we imagined that a regioselective carbometallation of the pendant olefin could afford 3 , which upon endocyclic β-hydride elimination 13,14 would lead to the unprecedented cyclohexene 4 (Figure 1c-route A). Carbometallation could occur with the opposite regioselectivity to generate 5 , which upon reductive elimination would yield bicyclic heptanones 6 (Figure 1c-route B).…”
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“…Next, we imagined that a regioselective carbometallation of the pendant olefin could afford 3 , which upon endocyclic β-hydride elimination 13,14 would lead to the unprecedented cyclohexene 4 (Figure 1c-route A). Carbometallation could occur with the opposite regioselectivity to generate 5 , which upon reductive elimination would yield bicyclic heptanones 6 (Figure 1c-route B).…”
mentioning
confidence: 99%
“…Carbometallation could occur with the opposite regioselectivity to generate 5 , which upon reductive elimination would yield bicyclic heptanones 6 (Figure 1c-route B). 15a On the basis of our previous study, 13 we realized that the key challenge would be to identify a catalyst to favor the proposed cycloisomerization, in preference to the known hydroacylation and carboacylation 15 pathways.…”
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