Stereospecific photochemical ring expansion of lithiated benzamides

Journal of the American Chemical Society

Volumn 125, Issue 31, 2003, Pages 9278-9279

  Clayden, Jonathan ^a   Knowles, Faye E ^a   Menet, Christel J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE; CYCLOHEPTANE DERIVATIVE; LITHIUM DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; PHOTOCHEMISTRY; PROTON TRANSPORT; REACTION ANALYSIS; STEREOSPECIFICITY; X RAY DIFFRACTION;

EID: 0042709602     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035827i     Document Type: Article

References (22)

1. Mander, L. N. Synlett 1991, 134. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 729 and references therein.
2. Mander, L. N. Synlett 1991, 134. Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 729 and references therein.
3. Wender, P. A.; Dore, T. M. In Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Raton, FL, 1994; p 280.
4. Ahmed, A.; Clayden, J.; Yasin, S. A. Chem. Commun. 1999, 231.
5. Clayden, J.; Menet, C. J.; Mansfield, D. J. Org. Lett. 2000, 2, 4229. Clayden, J.; Tchabanenko, K.; Yasin, S. A.; Turnbull, M. D. Synlett 2001, 302
6. Clayden, J.; Menet, C. J.; Mansfield, D. J. Org. Lett. 2000, 2, 4229. Clayden, J.; Tchabanenko, K.; Yasin, S. A.; Turnbull, M. D. Synlett 2001, 302
7. Clayden, J.; Menet, C. J.; Mansfield, D. J. Chem. Commun. 2002, 38.
8. Clayden, J.; Knowles, F. E.; Menet, C. J. Tetrahedron Lett. 2003, 44, 3397.
9. The absolute stereochemistry of 16-18 is deduced from the retentive stereospecificity of the cyclization of 13e: see ref 6.
10. Protonation of the enolate 7 derived by cyclization of 6a indicates that it is formed as a mixture of diastereoisomers, so at least in this case the rearrangement must be stereoselective and not simply stereospecific.
11. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
12. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
13. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
14. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
15. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
16. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
17. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
18. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
19. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976, Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970. This rearrangement can be viewed as a reverse aza-vinylcyclopropane rearrangement (Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 899. Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174. Cloke, J. B.; Maginnity, P. M. J. Am. Chem. Soc. 1951, 73, 49. Ellis, M. C.; Stevens, R. V. Tetrahedron Lett. 1967, 5185). For other photochemical N → C rearrangements, see: Archier-Jay, D.; Besbes, N.; Laurent, A.; Laurent, E.; Lesniak, S.; Tardivel, R. Bull. Soc. Chim. Fr. 1989, 537. Amougay, A.; Letsch, O.; Pete, J.-P.; Piva, O. Tetrahedron 1996, 52, 2405. Becker, H.-D.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1983, 36, 2073.
20. Berson, J. A. Acc. Chem. Res. 1972, 5, 406.
21. Such rearrangements are notoriously disrespectful of the Woodward-Hoffmann rules, see: Klärner, F.-G. Angew. Chem., Int. Ed. Engl. 1974, 13, 268. Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1974, 96, 2857.
22. Such rearrangements are notoriously disrespectful of the Woodward-Hoffmann rules, see: Klärner, F.-G. Angew. Chem., Int. Ed. Engl. 1974, 13, 268. Baldwin, J. E.; Broline, B. M. J. Am. Chem. Soc. 1974, 96, 2857.