Phospho-transfer catalysis on the asymmetric hydrophosphonylation of aldehydes

Journal of Organometallic Chemistry

Volumn 550, Issue 1-2, 1998, Pages 29-57

  Davies, Stephen R ^a   Mitchell, Michael C ^a   Cain, Christopher P ^a   Devitt, Paul G ^a   Taylor, Roger J ^b   Kee, Terence P ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b Ciba Geigy PLC   (United Kingdom)

Author keywords

Absolute configuration; Amphoteric catalysts; Chiral derivatising agent; Configurational stability; Enantiopurity assay; Enantioselective; Metal complexes; Pudovik reaction

Indexed keywords

RHIZOPUS ORYZAE;

EID: 0002042160     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(97)00176-9     Document Type: Article

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21. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
22. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
23. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
24. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
25. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
26. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
27. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
28. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
29. For leading references see, J.G. Allen, F.R. Atherton, M.J. Hall, C.H. Hassall, S.W. Holmes, R.W. Lambert, L.J. Nisbet, P.S. Ringrose, Nature 272 (1978) 56; L. Cheng, C.A. Goodwin, M.F. Scully, V.V. Kakkar, G. Claeson, Tetrahedron Lett. 32 (1991) 7333; J. Med. Chem. 35 (1992) 3364; C-L.J. Wang, T.L. Taylor, A.J. Mical, S. Spitz, T.M. Reilly, Tetrahedron Lett. 33 (1992) 7667; D. Green, G. Patel, S. Engendy, J.A. Baban, G. Claeson, V.V. Kakkar, J. Deadman, Tetrahedron Lett. 34 (1993) 6917; Tetrahedron 50 (1994) 5099; R. Shankar, A.I. Scott, Tetrahedron Lett. 34 (1993) 231; C. Chengzhi, D. Buechler, D. Lowe, S. Urwyler, G. Shapiro, Tetrahedron 50 (1994) 5735; M. Nomizu, A. Otaka, T.R. Burke Jr., P.P. Roller, Tetrahedron, 50 (1994) 2691; O.M. Green, Tetrahedron Lett. 35 (1994) 8081; V. Ojea, M. Ruiz, G. Shapiro, E. Pombo-Villar, Tetrahedron Lett. 35 (1994) 3273; M. Mahajna, E. Breuer, J. Chem. Soc. Perkin Trans. I, (1994) 1847; B. Yi, T.R. Burke Jr., Tetrahedron Lett. 36 (1995) 4733; D.B. Berkowitz, M.K. Smith, J. Org. Chem. 60 (1995) 1233; J-M. Campagne, J. Coste, P. Jouin, Tetrahedron Lett. 36 (1995) 2079; J. Deadman, G. Claeson, M.F. Scully, J. Enzym. Inhib. 9 (1995) 29; J. Deadman, S. Engendy, C.A. Goodwin, D. Green, J.A. Baban, G. Patel, E. Skordalakes, N. Chino, G. Claeson, V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511; V.V. Kakkar, M.F. Scully, J. Med. Chem. 38 (1995) 1511
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108. See for example, M.T.P. Viet, V. Sharma, J.D. Wuest, Inorg. Chem. 30 (1991) 3026; F.B-Gariepy, K. Hoogsteen, V. Sharma, J.D. Wuest, Inorg. Chem. 30 (1991) 4140; T. Bach, D.N.A. Fox, M.T. Reetz, J. Chem. Soc. Chem. Commun. (1992) 1634; V. Sharma, M. Simard, J.D. Wuest, J. Am. Chem. Soc. 114 (1992) 7931; M. Simard, J. Vaugeois, J.D. Wuest, J. Am. Chem. Soc. 115 (1993) 370.
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110. See for example, M.T.P. Viet, V. Sharma, J.D. Wuest, Inorg. Chem. 30 (1991) 3026; F.B-Gariepy, K. Hoogsteen, V. Sharma, J.D. Wuest, Inorg. Chem. 30 (1991) 4140; T. Bach, D.N.A. Fox, M.T. Reetz, J. Chem. Soc. Chem. Commun. (1992) 1634; V. Sharma, M. Simard, J.D. Wuest, J. Am. Chem. Soc. 114 (1992) 7931; M. Simard, J. Vaugeois, J.D. Wuest, J. Am. Chem. Soc. 115 (1993) 370.
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