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Volumn 349, Issue 7, 2007, Pages 1185-1198

An unprecedented rhodium-catalyzed asymmetric intermolecular hydroacylation reaction with salicylaldehydes

Author keywords

Asymmetric catalysis; C H activation; Phosphane ligands; Phosphites; Phosphoramidites; Rhodium

Indexed keywords


EID: 34547213920     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600583     Document Type: Article
Times cited : (129)

References (68)
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    • Recently, a chelation-assisted intramolecular hydroacylation using a (butenylsulfanyl)benzaldehyde yielding medium-sized heterocycles has been developed, see: H. D. Bendorf, C. M. Colella, E. C. Dixon, M. Marchetti, A. N. Matukonis, J. D. Musselman, T. A. Tiley, Tetrahedron Lett. 2002, 43, 7031-7034.
    • Recently, a chelation-assisted intramolecular hydroacylation using a (butenylsulfanyl)benzaldehyde yielding medium-sized heterocycles has been developed, see: H. D. Bendorf, C. M. Colella, E. C. Dixon, M. Marchetti, A. N. Matukonis, J. D. Musselman, T. A. Tiley, Tetrahedron Lett. 2002, 43, 7031-7034.
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    • These ligands (except phosphoramidite 19, see Experimental Section) are either commercially available (8, 16, 17, 25 and 27) and/or were prepared following literature procedures; for 9, 16, 17 and 18: a) A. H. M. de Vries, A. Meetsma, B. L. Feringa, Angew. Chem. 1996, 108, 2526-2528;
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    • An alternative explanation could be that in the case of bidentate (and sterically demanding) ligands the coordination of norbornadiene to rhodium might be inhibited completely and therefore the attack of the free norbornadiene would proceed in an exo-like fashion
    • An alternative explanation could be that in the case of bidentate (and sterically demanding) ligands the coordination of norbornadiene to rhodium might be inhibited completely and therefore the attack of the free norbornadiene would proceed in an exo-like fashion.


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