Acyclic stereocontrol in radical reactions. Diastereoselective radical addition/allylation of N-propenoyloxazolidinone

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6090-6091

  Sibi, Mukund P ^a   Ji, Jianguo ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029814298     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960947c     Document Type: Article

References (42)

1. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
2. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
3. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
4. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
5. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
6. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
7. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
8. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
9. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
10. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
11. For selected recent examples on the use of Lewis acids in radical reactions see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. (d) Urabe, H.; Yamashita, K.; Suzuki, K; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576. (e) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481. (f) Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701. (g) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (h) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (i) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (j) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (k) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
12. For discussion on acyclic diastereoselection in radical reactions see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Giese, B. Radical in Organic Synthesis. Formation of Carbon-Carbon Bond; Pergamon: Oxford, 1986. (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (d) Smadja, W. Synlett 1994, 1. (e) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (f) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
13. For discussion on acyclic diastereoselection in radical reactions see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Giese, B. Radical in Organic Synthesis. Formation of Carbon-Carbon Bond; Pergamon: Oxford, 1986. (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (d) Smadja, W. Synlett 1994, 1. (e) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (f) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
14. For discussion on acyclic diastereoselection in radical reactions see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Giese, B. Radical in Organic Synthesis. Formation of Carbon-Carbon Bond; Pergamon: Oxford, 1986. (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (d) Smadja, W. Synlett 1994, 1. (e) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (f) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
15. For discussion on acyclic diastereoselection in radical reactions see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Giese, B. Radical in Organic Synthesis. Formation of Carbon-Carbon Bond; Pergamon: Oxford, 1986. (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (d) Smadja, W. Synlett 1994, 1. (e) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (f) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
16. For discussion on acyclic diastereoselection in radical reactions see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Giese, B. Radical in Organic Synthesis. Formation of Carbon-Carbon Bond; Pergamon: Oxford, 1986. (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (d) Smadja, W. Synlett 1994, 1. (e) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (f) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
17. For discussion on acyclic diastereoselection in radical reactions see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Giese, B. Radical in Organic Synthesis. Formation of Carbon-Carbon Bond; Pergamon: Oxford, 1986. (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (d) Smadja, W. Synlett 1994, 1. (e) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (f) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
18. Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779.
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21. (a) Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181.
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30. For selected examples of tandem radical additions from other laboratories see: (a) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288. (b) Boger, D. L.; Mathvink, R. J. J. Am. Chem. Soc. 1990, 112, 4003. (c) Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J. Am. Chem. Soc. 1995, 117, 4183.
31. For selected examples of tandem radical additions from other laboratories see: (a) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288. (b) Boger, D. L.; Mathvink, R. J. J. Am. Chem. Soc. 1990, 112, 4003. (c) Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J. Am. Chem. Soc. 1995, 117, 4183.
32. For selected examples of tandem radical additions from other laboratories see: (a) Mizuno, K.; Ikeda, M.; Toda, S.; Otsuji, Y. J. Am. Chem. Soc. 1988, 110, 1288. (b) Boger, D. L.; Mathvink, R. J. J. Am. Chem. Soc. 1990, 112, 4003. (c) Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J. Am. Chem. Soc. 1995, 117, 4183.
33. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
34. Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190.
35. (a) Use of an oxazolidinone auxiliary for addition/trapping with insignificant diastereoselectivity has been reported by Crich and Davies: Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. (b) While this manuscript was under preparation, another report on radical addition to N-enoyloxazolidinones with low selectivity was reported: Wu, M.-J.; Fu, C.-L.; Duh, T.-H.; Yeh, J.-Y. Synthesis 1996, 462.
36. (a) Use of an oxazolidinone auxiliary for addition/trapping with insignificant diastereoselectivity has been reported by Crich and Davies: Crich, D.; Davies, J. W. Tetrahedron Lett. 1987, 28, 4205. (b) While this manuscript was under preparation, another report on radical addition to N-enoyloxazolidinones with low selectivity was reported: Wu, M.-J.; Fu, C.-L.; Duh, T.-H.; Yeh, J.-Y. Synthesis 1996, 462.
37. 2 was finally added via syringe over 2 h.
38. For the preparation of the oxazolidinone derived from diphenylalanine see: Sibi, M. P.; Deshpande, P. K.; La Loggia, A. J.; Christensen, J. W. Tetrahedron Lett. 1995, 36, 8961.
39. 3)] (lit.: Hauck, R.-S.; Nau, H. Toxicol. Lett. 1989, 49, 41. Porubek, D. J.; Barnes, H.; Theodore, L. J.; Baillie, T. A. Chem. Res. Toxicol. 1988, 1, 343). All the other compounds were assumed to provide similar absolute stereochemistry at the newly formed center.
40. 3)] (lit.: Hauck, R.-S.; Nau, H. Toxicol. Lett. 1989, 49, 41. Porubek, D. J.; Barnes, H.; Theodore, L. J.; Baillie, T. A. Chem. Res. Toxicol. 1988, 1, 343). All the other compounds were assumed to provide similar absolute stereochemistry at the newly formed center.
41. For examples of acyl radical additions to enoates see: Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
42. The addition of acyl and alkoxyalkyl radicals to 1 in the absence of Lewis acids gave very low diastereoselectivity.