Totally stereoselective P-O to P-C migration rearrangement: Application to the synthesis of new chiral O-hydroxyaryl phosphine oxides

Chemistry - A European Journal

Volumn 4, Issue 6, 1998, Pages 1061-1067

  Legrand, Olivier ^a   Brunel, Jean Michel ^a   Constantieux, Thierry ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Asymmetric synthesis; Chirality; Phosphane oxides; Reaction mechanisms; Rearrangements

Indexed keywords

EID: 0031803655     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19980615)4:6<1061::AID-CHEM1061>3.0.CO;2-V     Document Type: Article

References (71)

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46. Recently, the synthesis of isolable 1,2-oxaphosphetanes has been achieved and X-ray crystallographic analysis have been performed to determine the structure of such compounds. See: a) T. Kawashima, K. Kato, R. Okazaki, Angew. Chem. 1993, 105, 941; Angew. Chem. Int. Ed. Engl. 1993, 32, 869; b) T. Kawashima, K. Kato, R. Okazaki, J. Am. Chem. Soc. 1992, 114, 4008.
47. Recently, the synthesis of isolable 1,2-oxaphosphetanes has been achieved and X-ray crystallographic analysis have been performed to determine the structure of such compounds. See: a) T. Kawashima, K. Kato, R. Okazaki, Angew. Chem. 1993, 105, 941; Angew. Chem. Int. Ed. Engl. 1993, 32, 869; b) T. Kawashima, K. Kato, R. Okazaki, J. Am. Chem. Soc. 1992, 114, 4008.
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54. Nevertheless, in any case turnstile rotation must be taken into consideration as a mechanistic alternative. See: a) P. Gillespie, P. Hoffmann, H. Klusacek, D. Marquarding, S. Pfohl, F. Ramirez, E. A. Tsolis, I. Ugi, Angew. Chem. 1971, 83, 691; Angew. Chem. Int. Ed. Engl. 1971, 10, 687;
55. Nevertheless, in any case turnstile rotation must be taken into consideration as a mechanistic alternative. See: a) P. Gillespie, P. Hoffmann, H. Klusacek, D. Marquarding, S. Pfohl, F. Ramirez, E. A. Tsolis, I. Ugi, Angew. Chem. 1971, 83, 691; Angew. Chem. Int. Ed. Engl. 1971, 10, 687;
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59. Previous investigations have been carried out on the sterochemical behavior of the four-membered oxyphosphoranes (1,2-oxaphosphetanes) which have three P-C bonds. See: a) F. Ramirez, J. F. Pilot, O. P. Madan, C. P. Smith, J. Am. Chem. Soc. 1968, 90, 1275; b) F. Ramirez, C. P. Smith, J. F. Pilot, ibid. 1968, 90, 6726; c) D. B. Denney, D. Z. Denney, C. D. Hall, K. L. Marsi, ibid. 1972, 94, 245; d) See also ref. [23] for a recent and pertinent study of the spiro-oxaphosphetane pseudorotation.
60. Previous investigations have been carried out on the sterochemical behavior of the four-membered oxyphosphoranes (1,2-oxaphosphetanes) which have three P-C bonds. See: a) F. Ramirez, J. F. Pilot, O. P. Madan, C. P. Smith, J. Am. Chem. Soc. 1968, 90, 1275; b) F. Ramirez, C. P. Smith, J. F. Pilot, ibid. 1968, 90, 6726; c) D. B. Denney, D. Z. Denney, C. D. Hall, K. L. Marsi, ibid. 1972, 94, 245; d) See also ref. [23] for a recent and pertinent study of the spiro-oxaphosphetane pseudorotation.
61. Previous investigations have been carried out on the sterochemical behavior of the four-membered oxyphosphoranes (1,2-oxaphosphetanes) which have three P-C bonds. See: a) F. Ramirez, J. F. Pilot, O. P. Madan, C. P. Smith, J. Am. Chem. Soc. 1968, 90, 1275; b) F. Ramirez, C. P. Smith, J. F. Pilot, ibid. 1968, 90, 6726; c) D. B. Denney, D. Z. Denney, C. D. Hall, K. L. Marsi, ibid. 1972, 94, 245; d) See also ref. [23] for a recent and pertinent study of the spiro-oxaphosphetane pseudorotation.
62. Previous investigations have been carried out on the sterochemical behavior of the four-membered oxyphosphoranes (1,2-oxaphosphetanes) which have three P-C bonds. See: a) F. Ramirez, J. F. Pilot, O. P. Madan, C. P. Smith, J. Am. Chem. Soc. 1968, 90, 1275; b) F. Ramirez, C. P. Smith, J. F. Pilot, ibid. 1968, 90, 6726; c) D. B. Denney, D. Z. Denney, C. D. Hall, K. L. Marsi, ibid. 1972, 94, 245; d) See also ref. [23] for a recent and pertinent study of the spiro-oxaphosphetane pseudorotation.
63. -1). See: a) R. R. Holmes, J. Am. Chem. Soc. 1978, 100, 433; b) ref. [24], Table 1.7-1.9, pp. 35-89.
64. -1). See: a) R. R. Holmes, J. Am. Chem. Soc. 1978, 100, 433; b) ref. [24], Table 1.7-1.9, pp. 35-89.
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