Diastereo- and enantioselective synthesis of β-amino cyclic ethers via the intramolecular reaction of γ-alkoxyallylstannane with imine

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4901-4908

  Park, Jung Youl ^a   Kadota, Isao ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; ETHER DERIVATIVE; GAMMA ALKOXYALLYLSTANNIC ACID; IMINE; ORGANOTIN COMPOUND; PHENETHYLAMINE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033603376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9903398     Document Type: Article

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27. Diastereoselective addition of allylic metal compounds to chiral imines, prepared by the condensation of aldehyde with optically active amines has been reported, see: (a) Yamamoto, Y.; Shinji, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. (b) Yamamoto, Y.; Ito, W. Tetrahedron. 1988, 44, 5415. (c) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883. (d) Wu, M. J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340. (e) Bhuyan, P. J.; Prajapati, D.; Sandhu, J. S.; Tetrahedron Lett. 1993, 34, 7975. (f) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J Org. Chem. 1994, 59, 7766. (g) Hashimoto, Y.; Takaoki, K.; Sudo, A. Ogasawara, T.; Saigo, K. Chem. Lett. 1995, 235. (h) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136. Enantioselective addition of chiral allylboron reagents to achiral imines has been reported, see: (i) Watanabe, K; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry. 1996, 6, 1531.
28. Diastereoselective addition of allylic metal compounds to chiral imines, prepared by the condensation of aldehyde with optically active amines has been reported, see: (a) Yamamoto, Y.; Shinji, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. (b) Yamamoto, Y.; Ito, W. Tetrahedron. 1988, 44, 5415. (c) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883. (d) Wu, M. J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340. (e) Bhuyan, P. J.; Prajapati, D.; Sandhu, J. S.; Tetrahedron Lett. 1993, 34, 7975. (f) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J Org. Chem. 1994, 59, 7766. (g) Hashimoto, Y.; Takaoki, K.; Sudo, A. Ogasawara, T.; Saigo, K. Chem. Lett. 1995, 235. (h) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136. Enantioselective addition of chiral allylboron reagents to achiral imines has been reported, see: (i) Watanabe, K; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry. 1996, 6, 1531.
29. Diastereoselective addition of allylic metal compounds to chiral imines, prepared by the condensation of aldehyde with optically active amines has been reported, see: (a) Yamamoto, Y.; Shinji, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. (b) Yamamoto, Y.; Ito, W. Tetrahedron. 1988, 44, 5415. (c) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883. (d) Wu, M. J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340. (e) Bhuyan, P. J.; Prajapati, D.; Sandhu, J. S.; Tetrahedron Lett. 1993, 34, 7975. (f) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J Org. Chem. 1994, 59, 7766. (g) Hashimoto, Y.; Takaoki, K.; Sudo, A. Ogasawara, T.; Saigo, K. Chem. Lett. 1995, 235. (h) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136. Enantioselective addition of chiral allylboron reagents to achiral imines has been reported, see: (i) Watanabe, K; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry. 1996, 6, 1531.
30. Diastereoselective addition of allylic metal compounds to chiral imines, prepared by the condensation of aldehyde with optically active amines has been reported, see: (a) Yamamoto, Y.; Shinji, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. (b) Yamamoto, Y.; Ito, W. Tetrahedron. 1988, 44, 5415. (c) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883. (d) Wu, M. J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340. (e) Bhuyan, P. J.; Prajapati, D.; Sandhu, J. S.; Tetrahedron Lett. 1993, 34, 7975. (f) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J Org. Chem. 1994, 59, 7766. (g) Hashimoto, Y.; Takaoki, K.; Sudo, A. Ogasawara, T.; Saigo, K. Chem. Lett. 1995, 235. (h) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136. Enantioselective addition of chiral allylboron reagents to achiral imines has been reported, see: (i) Watanabe, K; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry. 1996, 6, 1531.
31. Diastereoselective addition of allylic metal compounds to chiral imines, prepared by the condensation of aldehyde with optically active amines has been reported, see: (a) Yamamoto, Y.; Shinji, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. (b) Yamamoto, Y.; Ito, W. Tetrahedron. 1988, 44, 5415. (c) Laschat, S.; Kunz, H. J. Org. Chem. 1991, 56, 5883. (d) Wu, M. J.; Pridgen, L. N. J. Org. Chem. 1991, 56, 1340. (e) Bhuyan, P. J.; Prajapati, D.; Sandhu, J. S.; Tetrahedron Lett. 1993, 34, 7975. (f) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J Org. Chem. 1994, 59, 7766. (g) Hashimoto, Y.; Takaoki, K.; Sudo, A. Ogasawara, T.; Saigo, K. Chem. Lett. 1995, 235. (h) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136. Enantioselective addition of chiral allylboron reagents to achiral imines has been reported, see: (i) Watanabe, K; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry. 1996, 6, 1531.
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33. γ-Alkoxyallylstannane 5 was used for further reaction immediately after the reaction of the aldehyde precursor with (R)-(+)-1-phenylethylamine, since it decomposed very readily upon treatment with silica gel column.
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49. Titanium(IV)-1,1′-bi-2-naphthol complexs were used in some asymmetric reactions: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571. (d) Ganthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (e) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095.
50. Titanium(IV)-1,1′-bi-2-naphthol complexs were used in some asymmetric reactions: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571. (d) Ganthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (e) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095.
51. Titanium(IV)-1,1′-bi-2-naphthol complexs were used in some asymmetric reactions: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571. (d) Ganthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (e) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095.
52. Titanium(IV)-1,1′-bi-2-naphthol complexs were used in some asymmetric reactions: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571. (d) Ganthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (e) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095.
53. Titanium(IV)-1,1′-bi-2-naphthol complexs were used in some asymmetric reactions: (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571. (d) Ganthier, D. R., Jr.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (e) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095.
54. A referee suggested the interaction between the oxygen atom of substrates and Lewis acids may be responsible for the differences in enantioselectivity observed for 8a (Table 4, entry4, ee: 37%) and dimethyl derivative 36 (Table 5, entry 3, ee: 93%). This is a plausible explanation for the differences, but the results in the carbon series were not available and therefore we cannot discuss such an interaction at the present time.