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Volumn 350, Issue 18, 2008, Pages 2893-2902

Ligand control in enantioselective desymmetrization of bicyclic hydrazines: Rhodium(I)-catalyzed ring-opening versus hydroarylation

Author keywords

Asymmetric catalysis; C H activation; Desymmetrization; Ferrocene ligands; Rhodium

Indexed keywords


EID: 57849088665     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800587     Document Type: Article
Times cited : (76)

References (63)
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    • In previous work, we observed that organoboron reagents add to the alkene of diazabicycle 1 without ringopening: aM. Lautens, J.J. Mancuso, J. Org. Chem. 2004, 69, 3478;
    • In previous work, we observed that organoboron reagents add to the alkene of diazabicycle 1 without ringopening: a)M. Lautens, J.J. Mancuso, J. Org. Chem. 2004, 69, 3478;
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    • An analogous reductive arylation was observed in the ring-opening of oxa- and azanorbornenes, but separation of the products was not possible: C. J. Dockendorff, PhD thesis, University of Toronto, Canada, 2006;
    • a) An analogous reductive arylation was observed in the ring-opening of oxa- and azanorbornenes, but separation of the products was not possible: C. J. Dockendorff, PhD thesis, University of Toronto, (Canada), 2006;
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    • for an asymmetric hydroarylation of allenes with boronic acid, see
    • b) for an asymmetric hydroarylation of allenes with boronic acid, see : T. Nishimura, S. Hirabayashi, Y. Yasuhar, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 2556;
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    • for an asymmetric Pd-mediated hydroarylation of norbornene, see: X.-Y. Wu, H.-D. Xu, Q.-L. Zhou A. S. C. Chan, Tetrahedron: Asymmetry 2000, 11, 1255.
    • c) for an asymmetric Pd-mediated hydroarylation of norbornene, see: X.-Y. Wu, H.-D. Xu, Q.-L. Zhou A. S. C. Chan, Tetrahedron: Asymmetry 2000, 11, 1255.
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    • [3] for an experimental procedure. [14] a F. Menard, T. M. Chapman, C. Dockendorff, M. Lautens, Org. Lett. 2006, 8, 4569.
    • [3] for an experimental procedure. [14] a) F. Menard, T. M. Chapman, C. Dockendorff, M. Lautens, Org. Lett. 2006, 8, 4569.
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    • P-Phos based ligands: J. Wu, A. S. C. Chan, Acc. Chem. Res. 2006, 39, 711.
    • P-Phos based ligands: J. Wu, A. S. C. Chan, Acc. Chem. Res. 2006, 39, 711.
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    • Josiphos ligands: H.-U. Blaser, W. Brieden, B. Pugin, F. Spindler, M. Struder, A. Togni, Top. Catal. 2002, 19, 3.
    • Josiphos ligands: H.-U. Blaser, W. Brieden, B. Pugin, F. Spindler, M. Struder, A. Togni, Top. Catal. 2002, 19, 3.
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    • Difuorphos ligand: S. Jeulin, S. Duprat de Paule, V. Ratovelomanana- Vidal, J. P. Genet, N. Champion, P. Dellis, Angew. Chem. 2004, 116, 324;
    • Difuorphos ligand: S. Jeulin, S. Duprat de Paule, V. Ratovelomanana- Vidal, J. P. Genet, N. Champion, P. Dellis, Angew. Chem. 2004, 116, 324;
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    • [4c]
    • [4c]
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    • In cases where the boronic acid was insoluble in toluene, a few drops (∼0.05 mL) of THF were added to the substrate solution until it became homogeneous. It should be noted that the reaction mixture was biphasic after addition of water.
    • In cases where the boronic acid was insoluble in toluene, a few drops (∼0.05 mL) of THF were added to the substrate solution until it became homogeneous. It should be noted that the reaction mixture was biphasic after addition of water.
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    • It should be noted that such reactivity may have been observed by Pineschi and co-workers but not investigated. See ref.[8b
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    • For a review on rhodium and palladium 1,4-shifts see
    • For a review on rhodium and palladium 1,4-shifts see: S. Ma, Z. Gu, Angew. Chem. 2005, 117, 7680;
    • (2005) Angew. Chem , vol.117 , pp. 7680
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    • When the 3-pyrrolylboronic acid was prepared from N-TIPS-3- bromopyrrole, the colorless crystalline solid decomposed under vacuum to give a brown liquid.
    • When the 3-pyrrolylboronic acid was prepared from N-TIPS-3- bromopyrrole, the colorless crystalline solid decomposed under vacuum to give a brown liquid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.