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(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.
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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.
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0001630820
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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.
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Kakinuma, K.1
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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.
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Kakinuma, K.1
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0027288055
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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.
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Eguchi, T.1
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0034728899
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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.
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Clayden, J.1
McCarthy, C.2
Cumming, J.G.3
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18
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0001923963
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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.
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Savage, I.1
Thomas, E.J.2
Wilson, P.D.3
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19
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0032562768
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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.
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Clayden, J.1
McCarthy, C.2
Cumming, J.G.3
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20
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0037154723
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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.
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Hung, S.-C.1
Wen, Y.F.2
Chang, J.-W.3
Liao, C.-C.4
Uang, B.J.5
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21
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For a review on chiral enolate equivalent, see: Spino, C. Org. Prep. Proced. Int. 2003, 35, 1-140.
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Spino, C.1
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22
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0033588390
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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.
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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
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23
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0033061777
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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.
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Synthesis
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Braibante, M.E.F.1
Braibante, H.S.2
Costenaro, E.R.3
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24
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0032483577
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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.
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Ghosh, A.K.1
Fidanze, S.2
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25
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0030858177
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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.
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Sibi, M.P.1
Lu, J.2
Edwards, J.3
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26
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0029563701
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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.
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Charette, A.B.1
Côté, B.2
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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.
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note
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See ref 5. The source of the cyclohexylmagnesium bromide or chloride was varied without success in this particular case.
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31
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4344565752
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note
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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.
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See, for example: Gryko, D.; Chalko, J.; Jurczak, J. Chirality 2003, 15, 514-541.
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3242745477
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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.
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Omote, Y.5
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0037189230
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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.
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0000762847
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Alexakis, A.; Gardette, M.; Colin, S. Tetrahedron Lett. 1988, 29, 2951-2954.
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