A Quantum Chemical Exploration of the Horner-Wadsworth-Emmons Reaction

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1280-1289

  Brandt, Peter ^a   Norrby, Per Ola ^b   Martin, Ivar ^c   Rein, Tobias ^a,d  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^d TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001109688     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971973t     Document Type: Article

References (80)

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2. For reviews, see: (a) Vedejs, E.; Peterson, M. J. Topics in Stereochemistry 1994, 27, 1-157. (b) Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 730-817. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. (Washington, B.C.) 1989, 89, 863-927. (d) Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: New York, 1979; pp 155-205, (e) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253. (f) Boutagy, J.; Thomas, R. Chem. Rev. (Washington, D.C.) 1974, 74, 87-99.
3. For reviews, see: (a) Vedejs, E.; Peterson, M. J. Topics in Stereochemistry 1994, 27, 1-157. (b) Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 730-817. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. (Washington, B.C.) 1989, 89, 863-927. (d) Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: New York, 1979; pp 155-205, (e) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253. (f) Boutagy, J.; Thomas, R. Chem. Rev. (Washington, D.C.) 1974, 74, 87-99.
4. For reviews, see: (a) Vedejs, E.; Peterson, M. J. Topics in Stereochemistry 1994, 27, 1-157. (b) Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 730-817. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. (Washington, B.C.) 1989, 89, 863-927. (d) Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: New York, 1979; pp 155-205, (e) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253. (f) Boutagy, J.; Thomas, R. Chem. Rev. (Washington, D.C.) 1974, 74, 87-99.
5. For reviews, see: (a) Vedejs, E.; Peterson, M. J. Topics in Stereochemistry 1994, 27, 1-157. (b) Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 730-817. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. (Washington, B.C.) 1989, 89, 863-927. (d) Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: New York, 1979; pp 155-205, (e) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253. (f) Boutagy, J.; Thomas, R. Chem. Rev. (Washington, D.C.) 1974, 74, 87-99.
6. For reviews, see: (a) Vedejs, E.; Peterson, M. J. Topics in Stereochemistry 1994, 27, 1-157. (b) Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 730-817. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. (Washington, B.C.) 1989, 89, 863-927. (d) Walker, B. J. In Organophosphorus Reagents in Organic Synthesis; Cadogan, J. I. G., Ed.; Academic Press: New York, 1979; pp 155-205, (e) Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253. (f) Boutagy, J.; Thomas, R. Chem. Rev. (Washington, D.C.) 1974, 74, 87-99.
7. Recent contributions: (a) Yamataka, H.; Takatsuka, T.; Hanafusa, T. J. Org. Chem. 1996, 61, 722-726. (b) Takeuchi, K.; Paschal, J. W.; Loncharich, R. J. J. Org. Chem. 1995, 60, 156-168. (c) Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080-10088. (d) Geletneky, C.; Försterling, F.-H.; Bock, W.; Berger, S. Chem. Ber. 1993, 126, 2397-2401.
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13. See also: (c) Kranz, M.; Denmark, S. E. J. Org. Chem. 1995, 60, 5867-5877, and references therein, (d) Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437-2447. For an example of modeling of an asymmetric HWE reaction by use of molecular mechanics calculations, see: (e) Narasaka, K.; Hidai, E.; Hayashi, Y.; Gras, J.-L. J. Chem. Soc., Chem. Commun. 1993, 102-104. For a calculational study of the Horner - Wittig reaction, see: (f) Armstrong, D. R.; Barr, D.; Davidson, M. G.; Hutton, G.; O'Brien, P.; Snaith, R.; Warren, S. J. Organomet. Chem. 1997, 529, 29-33.
14. See also: (c) Kranz, M.; Denmark, S. E. J. Org. Chem. 1995, 60, 5867-5877, and references therein, (d) Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437-2447. For an example of modeling of an asymmetric HWE reaction by use of molecular mechanics calculations, see: (e) Narasaka, K.; Hidai, E.; Hayashi, Y.; Gras, J.-L. J. Chem. Soc., Chem. Commun. 1993, 102-104. For a calculational study of the Horner - Wittig reaction, see: (f) Armstrong, D. R.; Barr, D.; Davidson, M. G.; Hutton, G.; O'Brien, P.; Snaith, R.; Warren, S. J. Organomet. Chem. 1997, 529, 29-33.
15. See also: (c) Kranz, M.; Denmark, S. E. J. Org. Chem. 1995, 60, 5867-5877, and references therein, (d) Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437-2447. For an example of modeling of an asymmetric HWE reaction by use of molecular mechanics calculations, see: (e) Narasaka, K.; Hidai, E.; Hayashi, Y.; Gras, J.-L. J. Chem. Soc., Chem. Commun. 1993, 102-104. For a calculational study of the Horner - Wittig reaction, see: (f) Armstrong, D. R.; Barr, D.; Davidson, M. G.; Hutton, G.; O'Brien, P.; Snaith, R.; Warren, S. J. Organomet. Chem. 1997, 529, 29-33.
16. See also: (c) Kranz, M.; Denmark, S. E. J. Org. Chem. 1995, 60, 5867-5877, and references therein, (d) Cramer, C. J.; Denmark, S. E.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437-2447. For an example of modeling of an asymmetric HWE reaction by use of molecular mechanics calculations, see: (e) Narasaka, K.; Hidai, E.; Hayashi, Y.; Gras, J.-L. J. Chem. Soc., Chem. Commun. 1993, 102-104. For a calculational study of the Horner - Wittig reaction, see: (f) Armstrong, D. R.; Barr, D.; Davidson, M. G.; Hutton, G.; O'Brien, P.; Snaith, R.; Warren, S. J. Organomet. Chem. 1997, 529, 29-33.
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43. For reviews, see: (a) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. (Washington, D.C.) 1997, 97, 2341-2372. (b) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369-379. Recent examples: (c) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755. (d) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979-1982. (e) Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. (f) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375-6378. (g) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735-3738. (h) Abiko, A.; Masamune, S. Tetrahedron Lett 1996, 37, 1077-1080.
44. For reviews, see: (a) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. (Washington, D.C.) 1997, 97, 2341-2372. (b) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369-379. Recent examples: (c) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755. (d) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979-1982. (e) Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. (f) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375-6378. (g) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735-3738. (h) Abiko, A.; Masamune, S. Tetrahedron Lett 1996, 37, 1077-1080.
45. For reviews, see: (a) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. (Washington, D.C.) 1997, 97, 2341-2372. (b) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369-379. Recent examples: (c) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755. (d) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979-1982. (e) Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. (f) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375-6378. (g) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735-3738. (h) Abiko, A.; Masamune, S. Tetrahedron Lett 1996, 37, 1077-1080.
46. For reviews, see: (a) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. (Washington, D.C.) 1997, 97, 2341-2372. (b) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369-379. Recent examples: (c) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755. (d) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979-1982. (e) Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. (f) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375-6378. (g) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735-3738. (h) Abiko, A.; Masamune, S. Tetrahedron Lett 1996, 37, 1077-1080.
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48. For reviews, see: (a) Li, A.-H.; Dai, W.-M.; Aggarwal, V. K. Chem. Rev. (Washington, D.C.) 1997, 97, 2341-2372. (b) Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369-379. Recent examples: (c) Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755. (d) Dai, W.-M.; Wu, J.; Huang, X. Tetrahedron: Asymmetry 1997, 8, 1979-1982. (e) Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038. (f) Mendlik, M. T.; Cottard, M.; Rein, T.; Helquist, P. Tetrahedron Lett. 1997, 38, 6375-6378. (g) Tanaka, K.; Otsubo, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 3735-3738. (h) Abiko, A.; Masamune, S. Tetrahedron Lett 1996, 37, 1077-1080.
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55. B3LYP frequently gives an accuracy equal to or higher than MP2, both for ground and transition state properties: (a) Foresman, J. B.; Frisch, æ. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, 1996. (b) Frisch, M. J. Presentation at the 213th ACS National Meeting, San Fransisco, 1997. (c) Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 3385-3386.
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