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Volumn 6, Issue 16, 2004, Pages 2801-2804

A stereodivergent approach to amino acids, amino alcohols, or oxazolidinones of high enantiomeric purity

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMINOALCOHOL; OXAZOLIDINONE DERIVATIVE;

EID: 4344670098     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048936q     Document Type: Article
Times cited : (23)

References (40)
  • 1
    • 0028355337 scopus 로고
    • (a) For a review on synthetic methods of α-amino acids, see: Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650. (b) Williams, R. H. Synthesis of Optically Active α-Amino Acids; Pergamon Press: New York, 1989. (c) Schollkopf, U. Top. Curr. Chem. 1983, 109, 65-84.
    • (1994) Tetrahedron , vol.50 , pp. 1539-1650
    • Duthaler, R.O.1
  • 2
    • 0028355337 scopus 로고
    • Pergamon Press: New York
    • (a) For a review on synthetic methods of α-amino acids, see: Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650. (b) Williams, R. H. Synthesis of Optically Active α-Amino Acids; Pergamon Press: New York, 1989. (c) Schollkopf, U. Top. Curr. Chem. 1983, 109, 65-84.
    • (1989) Synthesis of Optically Active α-Amino Acids
    • Williams, R.H.1
  • 3
    • 0028355337 scopus 로고
    • (a) For a review on synthetic methods of α-amino acids, see: Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650. (b) Williams, R. H. Synthesis of Optically Active α-Amino Acids; Pergamon Press: New York, 1989. (c) Schollkopf, U. Top. Curr. Chem. 1983, 109, 65-84.
    • (1983) Top. Curr. Chem. , vol.109 , pp. 65-84
    • Schollkopf, U.1
  • 6
    • 0141992718 scopus 로고    scopus 로고
    • α,α-Dialkylated amino acids can be made from a related system. See: Spino, C.; Godbout, C. J. Am. Chem. Soc. 2003, 125, 12106-12107.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12106-12107
    • Spino, C.1    Godbout, C.2
  • 14
    • 0001630820 scopus 로고
    • For other related approaches, see: (a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160. (b) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804. (c) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4527-4540. (d) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283. (e) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291-3303. (f) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron: Asymmetry 1998, 9, 1427-1440. (g) Hung, S.-C.; Wen, Y. F.; Chang, J.-W.; Liao, C-C.; Uang, B. J. J. Org. Chem. 2002, 67, 1308-1313.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4157-4160
    • Kakinuma, K.1    Li, H.-Y.2
  • 15
    • 0025947588 scopus 로고
    • For other related approaches, see: (a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160. (b) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804. (c) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4527-4540. (d) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283. (e) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291-3303. (f) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron: Asymmetry 1998, 9, 1427-1440. (g) Hung, S.-C.; Wen, Y. F.; Chang, J.-W.; Liao, C-C.; Uang, B. J. J. Org. Chem. 2002, 67, 1308-1313.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 5801-5804
    • Kakinuma, K.1    Koudate, T.2    Li, H.-Y.3    Eguchi, T.4
  • 16
    • 0027288055 scopus 로고
    • For other related approaches, see: (a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160. (b) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804. (c) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4527-4540. (d) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283. (e) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291-3303. (f) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron: Asymmetry 1998, 9, 1427-1440. (g) Hung, S.-C.; Wen, Y. F.; Chang, J.-W.; Liao, C-C.; Uang, B. J. J. Org. Chem. 2002, 67, 1308-1313.
    • (1993) Tetrahedron , vol.49 , pp. 4527-4540
    • Eguchi, T.1    Koudate, T.2    Kakinuma, K.3
  • 17
    • 0034728899 scopus 로고    scopus 로고
    • For other related approaches, see: (a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160. (b) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804. (c) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4527-4540. (d) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283. (e) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291-3303. (f) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron: Asymmetry 1998, 9, 1427-1440. (g) Hung, S.-C.; Wen, Y. F.; Chang, J.-W.; Liao, C-C.; Uang, B. J. J. Org. Chem. 2002, 67, 1308-1313.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3279-3283
    • Clayden, J.1    McCarthy, C.2    Cumming, J.G.3
  • 18
    • 0001923963 scopus 로고    scopus 로고
    • For other related approaches, see: (a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160. (b) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804. (c) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4527-4540. (d) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283. (e) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291-3303. (f) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron: Asymmetry 1998, 9, 1427-1440. (g) Hung, S.-C.; Wen, Y. F.; Chang, J.-W.; Liao, C-C.; Uang, B. J. J. Org. Chem. 2002, 67, 1308-1313.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 3291-3303
    • Savage, I.1    Thomas, E.J.2    Wilson, P.D.3
  • 19
    • 0032562768 scopus 로고    scopus 로고
    • For other related approaches, see: (a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160. (b) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804. (c) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4527-4540. (d) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283. (e) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291-3303. (f) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron: Asymmetry 1998, 9, 1427-1440. (g) Hung, S.-C.; Wen, Y. F.; Chang, J.-W.; Liao, C-C.; Uang, B. J. J. Org. Chem. 2002, 67, 1308-1313.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1427-1440
    • Clayden, J.1    McCarthy, C.2    Cumming, J.G.3
  • 20
    • 0037154723 scopus 로고    scopus 로고
    • For other related approaches, see: (a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160. (b) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804. (c) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4527-4540. (d) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron Lett. 2000, 41, 3279-3283. (e) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291-3303. (f) Clayden, J.; McCarthy, C.; Cumming, J. G. Tetrahedron: Asymmetry 1998, 9, 1427-1440. (g) Hung, S.-C.; Wen, Y. F.; Chang, J.-W.; Liao, C-C.; Uang, B. J. J. Org. Chem. 2002, 67, 1308-1313.
    • (2002) J. Org. Chem. , vol.67 , pp. 1308-1313
    • Hung, S.-C.1    Wen, Y.F.2    Chang, J.-W.3    Liao, C.-C.4    Uang, B.J.5
  • 21
    • 0037301364 scopus 로고    scopus 로고
    • For a review on chiral enolate equivalent, see: Spino, C. Org. Prep. Proced. Int. 2003, 35, 1-140.
    • (2003) Org. Prep. Proced. Int. , vol.35 , pp. 1-140
    • Spino, C.1
  • 22
    • 0033588390 scopus 로고    scopus 로고
    • For selected examples of the use of Curtius or similar rearrangements in making amino acids, see: (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417. (b) Braibante, M. E. F.; Braibante, H. S.; Costenaro, E. R. Synthesis 1999, 943-947. (c) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152. (d) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872. (e) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732. (f) Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.
    • (1999) J. Org. Chem. , vol.64 , pp. 6411-6417
    • Evans, D.A.1    Wu, L.D.2    Wiener, J.J.M.3    Johnson, J.S.4    Ripin, D.H.B.5    Tedrow, J.S.6
  • 23
    • 0033061777 scopus 로고    scopus 로고
    • For selected examples of the use of Curtius or similar rearrangements in making amino acids, see: (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417. (b) Braibante, M. E. F.; Braibante, H. S.; Costenaro, E. R. Synthesis 1999, 943-947. (c) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152. (d) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872. (e) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732. (f) Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.
    • (1999) Synthesis , pp. 943-947
    • Braibante, M.E.F.1    Braibante, H.S.2    Costenaro, E.R.3
  • 24
    • 0032483577 scopus 로고    scopus 로고
    • For selected examples of the use of Curtius or similar rearrangements in making amino acids, see: (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417. (b) Braibante, M. E. F.; Braibante, H. S.; Costenaro, E. R. Synthesis 1999, 943-947. (c) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152. (d) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872. (e) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732. (f) Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.
    • (1998) J. Org. Chem. , vol.63 , pp. 6146-6152
    • Ghosh, A.K.1    Fidanze, S.2
  • 25
    • 0030858177 scopus 로고    scopus 로고
    • For selected examples of the use of Curtius or similar rearrangements in making amino acids, see: (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417. (b) Braibante, M. E. F.; Braibante, H. S.; Costenaro, E. R. Synthesis 1999, 943-947. (c) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152. (d) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872. (e) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732. (f) Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.
    • (1997) J. Org. Chem. , vol.62 , pp. 5864-5872
    • Sibi, M.P.1    Lu, J.2    Edwards, J.3
  • 26
    • 0029563701 scopus 로고
    • For selected examples of the use of Curtius or similar rearrangements in making amino acids, see: (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417. (b) Braibante, M. E. F.; Braibante, H. S.; Costenaro, E. R. Synthesis 1999, 943-947. (c) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152. (d) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872. (e) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732. (f) Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 12721-12732
    • Charette, A.B.1    Côté, B.2
  • 27
    • 0035917343 scopus 로고    scopus 로고
    • For selected examples of the use of Curtius or similar rearrangements in making amino acids, see: (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417. (b) Braibante, M. E. F.; Braibante, H. S.; Costenaro, E. R. Synthesis 1999, 943-947. (c) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152. (d) Sibi, M. P.; Lu, J.; Edwards, J. J. Org. Chem. 1997, 62, 5864-5872. (e) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732. (f) Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.
    • (2001) J. Org. Chem. , vol.66 , pp. 2667-2673
    • Tanaka, M.1    Oba, M.2    Tamai, K.3    Suemune, H.4
  • 30
    • 4344640033 scopus 로고    scopus 로고
    • note
    • See ref 5. The source of the cyclohexylmagnesium bromide or chloride was varied without success in this particular case.
  • 31
    • 4344565752 scopus 로고    scopus 로고
    • note
    • We have developed a resin-bound version of this chiral auxiliary. Patent 2,413,713 filed for Canada-U.S. in December 2003. Manuscript for publication in preparation.
  • 39
    • 0037189230 scopus 로고    scopus 로고
    • This method of oxidation has been shown to proceed without racemization of the amino acid. See: (a) Kashima, C.; Harada, K.; Fujioka, Y.; Maruyama, T.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1988, 535-539. (b) Dondoni, A.; Mariotti, G.; Marra, A. J. Org. Chem. 2002, 67, 4475-4486.
    • (2002) J. Org. Chem. , vol.67 , pp. 4475-4486
    • Dondoni, A.1    Mariotti, G.2    Marra, A.3


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