Diastereo- and enantioselective hydrodimerization of β-monosubstituted acrylic acid amides induced by chiral samarium(II) complexes

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7497-7500

  Kikukawa, Takashi ^a   Hanamoto, Takeshi ^a   Inanaga, Junji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; METAL COMPLEX; SAMARIUM; TERTIARY AMINE;

ARTICLE; DIASTEREOISOMER; DIMERIZATION; ENANTIOMER; STEREOCHEMISTRY;

EID: 0033570125     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01551-8     Document Type: Article

References (24)

1. For reviews, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995; (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969; (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; (d) Smadia, W. Synlett 1994, 1.
2. For reviews, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995; (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969; (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; (d) Smadia, W. Synlett 1994, 1.
3. For reviews, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995; (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969; (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; (d) Smadia, W. Synlett 1994, 1.
4. For reviews, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995; (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969; (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; (d) Smadia, W. Synlett 1994, 1.
5. For recent examples of the substrate-control, see: (a) Stack, J. G.; Curran, D. P.; Rebek Jr., J.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918; (b) Porter, N. A.; Rosensteine, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W. X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664; (c) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421; (d) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779; (e) Fukuzawa, S.; Seki, K.; Tatsukawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482.
6. For recent examples of the substrate-control, see: (a) Stack, J. G.; Curran, D. P.; Rebek Jr., J.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918; (b) Porter, N. A.; Rosensteine, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W. X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664; (c) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421; (d) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779; (e) Fukuzawa, S.; Seki, K.; Tatsukawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482.
7. For recent examples of the substrate-control, see: (a) Stack, J. G.; Curran, D. P.; Rebek Jr., J.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918; (b) Porter, N. A.; Rosensteine, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W. X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664; (c) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421; (d) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779; (e) Fukuzawa, S.; Seki, K.; Tatsukawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482.
8. For recent examples of the substrate-control, see: (a) Stack, J. G.; Curran, D. P.; Rebek Jr., J.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918; (b) Porter, N. A.; Rosensteine, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W. X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664; (c) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421; (d) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779; (e) Fukuzawa, S.; Seki, K.; Tatsukawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482.
9. For recent examples of the substrate-control, see: (a) Stack, J. G.; Curran, D. P.; Rebek Jr., J.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918; (b) Porter, N. A.; Rosensteine, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W. X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664; (c) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421; (d) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779; (e) Fukuzawa, S.; Seki, K.; Tatsukawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482.
10. For recent examples of the substrate-control, see: (a) Stack, J. G.; Curran, D. P.; Rebek Jr., J.; Ballester, P. J. Am. Chem. Soc. 1991, 113, 5918; (b) Porter, N. A.; Rosensteine, I. J.; Breyer, R. A.; Bruhnke, J. D.; Wu, W. X.; McPhail, A. T. J. Am. Chem. Soc. 1992, 114, 7664; (c) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421; (d) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779; (e) Fukuzawa, S.; Seki, K.; Tatsukawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482.
11. For recent examples of the catalyst-control, see: (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576; (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481; (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029; (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200; (e) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800; (f) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. For the ligand control, see: Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
12. For recent examples of the catalyst-control, see: (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576; (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481; (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029; (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200; (e) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800; (f) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. For the ligand control, see: Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
13. For recent examples of the catalyst-control, see: (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576; (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481; (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029; (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200; (e) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800; (f) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. For the ligand control, see: Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
14. For recent examples of the catalyst-control, see: (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576; (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481; (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029; (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200; (e) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800; (f) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. For the ligand control, see: Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
15. For recent examples of the catalyst-control, see: (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576; (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481; (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029; (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200; (e) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800; (f) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. For the ligand control, see: Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
16. For recent examples of the catalyst-control, see: (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576; (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481; (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029; (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200; (e) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800; (f) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. For the ligand control, see: Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
17. For recent examples of the catalyst-control, see: (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576; (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481; (c) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029; (d) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200; (e) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 3800; (f) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. For the ligand control, see: Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
18. A part of this work was presented at the 16th Meeting of the Rare Earth Society of Japan, Osaka, May, 1999.
19. 8-BINOL gave less satisfactory results. Also, the use of dilithium binaphthoxide (4 equiv.) in the presence of t-butanol in place of the BINOL-amine system afforded 2a with low ee (6%).
20. Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
21. (a) Inanaga, J.; Handa, Y.; Tabuchi, T.; Otsubo, K.; Yamaguchi, M.; Hanamoto, T. Tetrahedron Lett. 1991, 32, 6557; (b) Kanemasa, S.; Yamamoto, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 8505.
22. (a) Inanaga, J.; Handa, Y.; Tabuchi, T.; Otsubo, K.; Yamaguchi, M.; Hanamoto, T. Tetrahedron Lett. 1991, 32, 6557; (b) Kanemasa, S.; Yamamoto, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 8505.
23. No reaction took place at -78°C in the absence of amines.
24. As the chiral samarium complex gradually decomposed even at -78°C, an excess amount of the reagent was used.