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Asymmetric Rhodium-Directed anti-Markovnikov Regioselective Boracyclopentannulation

Momar Toure 1 Olivier Chuzel 1 Jean-Luc Parrain 1 
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : A Shimoi-type activation of B−H bond of NHC-boranes by a diphosphane-ligated cationic Rh complex was applied in an unprecedented intramolecular hydroboration reaction of simple olefins. The use of NHCboranes as hydroborating reagents is still undisclosed due to their nonreactivity toward alkenes which could be explained by the high stability of this complex rendering it unable to provide a "free" borane hydroborating reagent. B−H bond Rh activation of NHC-borane circumvents this limitation, and asymmetric Rh-directed anti-Markovnikov boracyclopentannulation reaction led to a library of enantioenriched cyclic boranes in high yield (up to 94%) with high regio- (up to 100%) and enantioselectivity (er up to 99.2:0.8). This new activation mode of NHCboranesn highlights their use in organometallic chemistry and offers a very good approach to access chiral cyclic NHC-boranes.
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Submitted on : Monday, March 18, 2013 - 4:59:14 PM
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Momar Toure, Olivier Chuzel, Jean-Luc Parrain. Asymmetric Rhodium-Directed anti-Markovnikov Regioselective Boracyclopentannulation. Journal of the American Chemical Society, American Chemical Society, 2012, 134, pp.17892-17895. ⟨10.1021/ja309018f⟩. ⟨hal-00801941⟩



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