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Volumn 8, Issue 12, 2013, Pages 3051-3062

Iron- and bismuth-catalyzed asymmetric mukaiyama aldol reactions in aqueous media

Author keywords

aldol reaction; asymmetric catalysis; bismuth; C C coupling; iron

Indexed keywords

ALDOL REACTIONS; ANHYDROUS CONDITIONS; ASYMMETRIC CATALYSIS; C-C COUPLING; COORDINATION ENVIRONMENT; DIASTEREO- AND ENANTIOSELECTIVITY; MUKAIYAMA ALDOL REACTION; VERY LOW TEMPERATURES;

EID: 84888377389     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201301149     Document Type: Article
Times cited : (48)

References (144)
  • 2
    • 11844259698 scopus 로고    scopus 로고
    • (Ed.: R. Mahrwald), Wiley-VCH, Weinheim
    • Modern Aldol Reactions (Ed.:, R. Mahrwald,), Wiley-VCH, Weinheim, 2004
    • (2004) Modern Aldol Reactions
  • 16
    • 0000699983 scopus 로고    scopus 로고
    • in (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 3
    • E. M. Carreira, in Comprehensive Asymmetric Catalysis (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Heidelberg, 1999, 3, 997-1065
    • (1999) Comprehensive Asymmetric Catalysis , pp. 997-1065
    • Carreira, E.M.1
  • 21
    • 0000699983 scopus 로고    scopus 로고
    • For the Mukaiyama aldol reaction, see:, In (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • For the Mukaiyama aldol reaction, see:, E. M. Carreira, In Comprehensive Asymmetric Catalysis I-III (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999, pp. 997-1065
    • (1999) Comprehensive Asymmetric Catalysis I-III , pp. 997-1065
    • Carreira, E.M.1
  • 23
    • 33644537576 scopus 로고    scopus 로고
    • in (Ed.: R. Mahrwald), Wiley-VCH, Weinheim, 1
    • T. Mukaiyama, J. I. Matsuo, in Modern Aldol Reactions (Ed.:, R. Mahrwald,), Wiley-VCH, Weinheim, 2004, 1, 127-160
    • (2004) Modern Aldol Reactions , pp. 127-160
    • Mukaiyama, T.1    Matsuo, J.I.2
  • 24
    • 33645855075 scopus 로고    scopus 로고
    • in (Ed.: R. Mahrwald), Wiley-VCH, Weinheim, 2.
    • K. Ishihara, H. Yamamoto, in Modern Aldol Reactions (Ed.:, R. Mahrwald,), Wiley-VCH, Weinheim, 2004, 2, 25-68.
    • (2004) Modern Aldol Reactions , pp. 25-68
    • Ishihara, K.1    Yamamoto, H.2
  • 27
    • 69249088448 scopus 로고    scopus 로고
    • For recent reports on asymmetric direct-type aldol reactions by using organocatalysts, see S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178-2189
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 2178-2189
    • Bertelsen, S.1    Jørgensen, K.A.2
  • 47
    • 0002950518 scopus 로고
    • (Ed.: A. E. Martell), ACS Monograph 168, American Chemical Society, Washington, DC.
    • Coordination Chemistry, Vol. 2 (Ed.:, A. E. Martell,), ACS Monograph 168, American Chemical Society, Washington, DC, 1978.
    • (1978) Coordination Chemistry, Vol. 2
  • 73
    • 83755196032 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 12262-12265.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 12262-12265
  • 75
    • 52649131306 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6909-6911.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6909-6911
  • 81
    • 0000727245 scopus 로고    scopus 로고
    • III, are known to promote the epimerization between syn- 3 a and anti- 3 a through keto-enolization, see.
    • III, are known to promote the epimerization between syn- 3 a and anti- 3 a through keto-enolization, see:, D. E. Ward, M. Sales, P. K. Sasmal, Org. Lett. 2001, 3, 3671-3673.
    • (2001) Org. Lett. , vol.3 , pp. 3671-3673
    • Ward, D.E.1    Sales, M.2    Sasmal, P.K.3
  • 83
    • 84875823478 scopus 로고    scopus 로고
    • For the use of Bi compounds in organic synthesis, see T. Ollevier, Org. Biomol. Chem. 2013, 11, 2740-2755
    • (2013) Org. Biomol. Chem. , vol.11 , pp. 2740-2755
    • Ollevier, T.1
  • 88
    • 48849106597 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4722-4724
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4722-4724
  • 90
    • 48749133072 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4719-4721
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4719-4721
  • 93
    • 53349159499 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 2082-2084.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 2082-2084
  • 103
    • 84888355991 scopus 로고    scopus 로고
    • -) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 108
    • 50249134990 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 1560-1638
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 1560-1638
  • 112
    • 18044370097 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2524-2527.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 2524-2527
  • 124
    • 0003181446 scopus 로고
    • (Ed.: J. D. Morrison), Academic Press, New York, Chapter 2
    • C. H. Heathcock, in Asymmetric Synthesis, Vol. 3, Part B (Ed.:, J. D. Morrison,), Academic Press, New York, 1984, Chapter 2.
    • (1984) Asymmetric Synthesis , vol.3 , Issue.PART B
    • Heathcock, C.H.1
  • 133
    • 0030913422 scopus 로고    scopus 로고
    • The enantiofacial differentiation of an aldehyde carbonyl group was trivial, owing to the relative preference of the carbonyl group that was coordinated by a Lewis acid for an (E)-configuration. One face of the aldehyde was shielded by the tert-butyl group of ligand L1 and the orientation of the aldehyde might be fixed by a hydrogen bond between the aldehyde and the hydroxy moieties of ligand L1. The formyl C - H×××O hydrogen bond is known to be important for fixing an aldehyde in chiral-Lewis-acid-catalyzed reactions, including the Mukaiyama aldol reaction; see.
    • The enantiofacial differentiation of an aldehyde carbonyl group was trivial, owing to the relative preference of the carbonyl group that was coordinated by a Lewis acid for an (E)-configuration. One face of the aldehyde was shielded by the tert-butyl group of ligand L1 and the orientation of the aldehyde might be fixed by a hydrogen bond between the aldehyde and the hydroxy moieties of ligand L1. The formyl C - H×××O hydrogen bond is known to be important for fixing an aldehyde in chiral-Lewis-acid-catalyzed reactions, including the Mukaiyama aldol reaction; see:, E. J. Corey, D. Barnes-Seeman, T. W. Lee, Tetrahedron Lett. 1997, 38, 4351-4354.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4351-4354
    • Corey, E.J.1    Barnes-Seeman, D.2    Lee, T.W.3
  • 135
    • 0000223871 scopus 로고
    • Furthermore, the rate acceleration and the stereochemical outcome in water bore a striking resemblance to that under high pressure. A curious coincidence between the reaction in water and that under high pressure has been observed in many reactions since, which is nowadays understood as a result of the high dielectric constant and the highest cohesive energy density (ced) of water; see
    • A. Lubineau, J. Org. Chem. 1986, 51, 2142-2144. Furthermore, the rate acceleration and the stereochemical outcome in water bore a striking resemblance to that under high pressure. A curious coincidence between the reaction in water and that under high pressure has been observed in many reactions since, which is nowadays understood as a result of the high dielectric constant and the highest cohesive energy density (ced) of water; see
    • (1986) J. Org. Chem. , vol.51 , pp. 2142-2144
    • Lubineau, A.1
  • 143
    • 84884490010 scopus 로고    scopus 로고
    • After submitting this manuscript, the following paper on the role of water in lanthanide-catalyzed Mukaiyama aldol reactions has been published:, 13972- 13979.
    • After submitting this manuscript, the following paper on the role of water in lanthanide-catalyzed Mukaiyama aldol reactions has been published:, M. Hatanaka, K. Morokuma, J. Am. Chem. Soc. 2013, 135, 13972- 13979.
    • (2013) J. Am. Chem. Soc. , pp. 135
    • Hatanaka, M.1    Morokuma, K.2
  • 144
    • 3442885636 scopus 로고    scopus 로고
    • The ced is often used as an indicator of entropy-driven aggregation and, thus, is experimentally proportional to "hydrophobicity"; see.
    • The ced is often used as an indicator of entropy-driven aggregation and, thus, is experimentally proportional to "hydrophobicity"; see:, G. Graziano, J. Chem. Phys. 2004, 121, 1878-1882.
    • (2004) J. Chem. Phys. , vol.121 , pp. 1878-1882
    • Graziano, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.