The Mechanism of Double Olefination Using Titanium-Substituted Ylides

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2574-2593

  Reynolds, Kelly A ^a   Finn, M G ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000881803     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9610016     Document Type: Article

References (122)

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57. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
58. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
59. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
60. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
61. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
62. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
63. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
64. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
65. For use of chiral ylides in the synthesis of enantiomerically enriched alkenes, see: (a) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034. (b) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1992, 114, 10674-10676. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700. (e) Bestmann, H. J.; Lienert, J. Angew. Chem., Int. Ed. Engl. 1969, 8, 763-764. (f) Tömösközi, I.; Janzso, G. Chem. Ind. (London) 1962, 2085-2086. (g) In a related reaction, optically active allenes were prepared using an ylide bearing a menthol substituent at the ylide carbon: Tömösközi, I.; Bestmann, H. J. Tetrahedron Lett. 1964, 20, 1293-1295. (h) See also: Stang, P. J.; Learned, A. E. J. Org. Chem. 1989, 54, 1779-1781. For enantioselective Wittig reactions within the confines of a chiral host, see: Toda, F.; Akai, H. J. Org. Chem. 1990, 55, 3446-3447.
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73. CP (90-100 Hz compared to 175 Hz).
74. The presence of electron-donating substituents on phosphorus is known to increase ylide nucleophilicity at carbon: (a) March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons, Inc.: New York, 1985; pp 850-851 and references therein. (b) Johnson, A. W.; LaCount, R. B. Chem. Ind. 1959, 52. Johnson, A. W.; LaCount, R. B. Tetrahedron 1960, 9, 130-138.
75. The presence of electron-donating substituents on phosphorus is known to increase ylide nucleophilicity at carbon: (a) March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons, Inc.: New York, 1985; pp 850-851 and references therein. (b) Johnson, A. W.; LaCount, R. B. Chem. Ind. 1959, 52. Johnson, A. W.; LaCount, R. B. Tetrahedron 1960, 9, 130-138.
76. The presence of electron-donating substituents on phosphorus is known to increase ylide nucleophilicity at carbon: (a) March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons, Inc.: New York, 1985; pp 850-851 and references therein. (b) Johnson, A. W.; LaCount, R. B. Chem. Ind. 1959, 52. Johnson, A. W.; LaCount, R. B. Tetrahedron 1960, 9, 130-138.
77. 2NP units is substantially more compressed than the others, as shown by the out-of-plane distances of each nitrogen center: 0.197 A° (N1), 0.218 A° (N2), and 0.022 A° (N3) A°. Interestingly, the atoms C6, C7, N3, P1, C1, and Ti lie in the same plane, and the thermal ellipsoids of the C6/C7/N3 dimethylamino unit are strongly elongated normal to this plane, perhaps indicating that the N3 pπ-orbital provides resonance donor stabilization to phosphonium-Ti fragment.
78. Vedejs, E.; Peterson, M. J. Topics Stereochem. 1994, 21, 1-157.
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80. (b) Mari, F.; Lahti, P. M.; McEwen, W. E. J. Am. Chem. Soc. 1992, 114, 813-821.
81. (c) Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3948-3958.
82. 17
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89. 3, giving rise to a Ti-substituted ylide species that lacks a chloride ligand on titanium, very low yields of vinylphosphonium salts are obtained.
90. 2 was found to be stable under inert atmosphere at room temperature for several months but "smokes" when exposed to air, which necessitated handling in the glove box. In comparison to most arylsubstituted phosphorus ylides, the amino substitution offers two practical advantages: the corresponding phosphine oxide, HMPA, is water soluble, and the greater reactivity of the starting phosphine, HMPT, makes the synthesis of precursor phosphonium salts extremely facile. Considering stereochemical outcome, ylide thermal stability, and isolability, these species appear to be best classified as stabilized to semistabilized ylides, but are much more basic than typical stabilized ylides that bear substituents to delocalize the negative charge on the ylide carbon.
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102. (a) Reference 23a; Chapter 9.
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120. Reference 23a, Chapter 9, pp 286-291, and references therein.
121. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1392, 57, 2768-2771.
122. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.