Hydrogen-bonding as a stereocontrolling element in free-radical C-allylation reactions: Vicinal, proximal, and remote asymmetric induction in the amino acid series

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2507-2508

  Hanessian, Stephen ^a   Yang, Hua ^a   Schaum, Robert ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029987866     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953913f     Document Type: Article

References (48)

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10. For recent examples in acyclic substrates with chiral auxilaries, see: (a) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohyake, Y.; Yamura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. (b) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. (c) Porter, N. A.; Rosenstein, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W.-X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664 and previous papers. (d) Hamon, D. P. G.; Massy-Westropp, R. A.; Razzino, P. J. Chem. Soc., Chem. Commun. 1991, 332; 722. (e) Giese, B.; Zehnder, M.; Roth, M. and Zeitz H.-G.J. Am. Chem. Soc. 1990, 112, 6741.
11. For recent examples in acyclic substrates with a chiral resident group, see: (a) Kundig, E. P.; Xu, L.-H.; Romanens P. Tetrahedron Lett. 1995, 36,4047. (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995. 481. (c) Giese, B.; Buliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. (d) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N. and Ogilvie, W. W. Synlett 1995, 449 and previous papers. (e) Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987. (g) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249. (h) Curran, D. P.; Abaraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4335.
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13. For recent examples in acyclic substrates with a chiral resident group, see: (a) Kundig, E. P.; Xu, L.-H.; Romanens P. Tetrahedron Lett. 1995, 36,4047. (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995. 481. (c) Giese, B.; Buliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. (d) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N. and Ogilvie, W. W. Synlett 1995, 449 and previous papers. (e) Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987. (g) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249. (h) Curran, D. P.; Abaraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4335.
14. For recent examples in acyclic substrates with a chiral resident group, see: (a) Kundig, E. P.; Xu, L.-H.; Romanens P. Tetrahedron Lett. 1995, 36,4047. (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995. 481. (c) Giese, B.; Buliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. (d) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N. and Ogilvie, W. W. Synlett 1995, 449 and previous papers. (e) Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. (f) Nagano, H.; Kuno, Y. J. Chem. Soc., Chem. Commun. 1994, 987. (g) Morikawa, T.; Washio, Y.; Shiro, M.; Taguchi, T. Chem. Lett. 1993, 249. (h) Curran, D. P.; Abaraham, A. C.; Liu, H. J. Org. Chem. 1991, 56, 4335.
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