2021
DOI: 10.1021/acs.organomet.0c00811
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Abstract: Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irrever… Show more

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Cited by 7 publications
(3 citation statements)
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“…exo-2-Alkenylnorbornanes were obtained from catalytic cross-hydroalkenylation of norbornenes with ethylene or ,-unsaturated carbonyls (like esters and amides) by using Ni, 31a,34 Ru, 35 or Ir (Scheme 4). 36 In the pioneering examples, the chemoselectivity and regioselectivity were controlled by distinct factors: (a) ringstrain relief after hydrometallation; (b) a polarized olefin that can facilitate the desired metallacycle formation with a reactive -CH for elimination; (c) alkenyl C-H activation and coordination of the carbonyl group to metal. These approaches effectively limited the problems related to the Scheme 3 NHC effects on catalytic regiodivergent cross-hydroalkenylation…”
Section: Account Synlettmentioning
confidence: 99%
“…exo-2-Alkenylnorbornanes were obtained from catalytic cross-hydroalkenylation of norbornenes with ethylene or ,-unsaturated carbonyls (like esters and amides) by using Ni, 31a,34 Ru, 35 or Ir (Scheme 4). 36 In the pioneering examples, the chemoselectivity and regioselectivity were controlled by distinct factors: (a) ringstrain relief after hydrometallation; (b) a polarized olefin that can facilitate the desired metallacycle formation with a reactive -CH for elimination; (c) alkenyl C-H activation and coordination of the carbonyl group to metal. These approaches effectively limited the problems related to the Scheme 3 NHC effects on catalytic regiodivergent cross-hydroalkenylation…”
Section: Account Synlettmentioning
confidence: 99%
“…The pioneering early work of Murai on linear-selective hydroarylation and Ellman and Bergman on enantioselective intramolecular cyclization have laid the foundation for this approach . Since then, significant advances have been made, in terms of both intramolecular and intermolecular enantioselective variants. …”
mentioning
confidence: 99%
“…Despite the progress made in this field of enantioselective alkene hydrocarbofunctionalization during the past decades, one prominent limitation is the scope of the alkenes. Currently, the alkenes are largely restricted to strained alkenes, conjugated alkenes, or functionalized alkenes. , Catalytic enantioselective intermolecular hydroarylation and hydroalkenylation of minimally polarized, unactivated α-olefins remains a long-standing challenge, due to the low reactivity of α-olefins and the formation of the usually favored linear product. Such examples are extremely scarce. Recently, a few catalytic systems have begun to emerge in this direction (Scheme A).…”
mentioning
confidence: 99%