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Volumn 39, Issue 38, 1998, Pages 6927-6930

1,5-asymmetric induction in addition reaction of aldehydes with chiral allyltitaniums having an amino group at the stereogenic center. Synthesis of optically active 2,6-cis-disubstituted piperidines

Author keywords

Amino alcohols; Asymmetric induction; Piperidines; Titanium and compounds

Indexed keywords

ALDEHYDE; GLUTARIMIDE DERIVATIVE; PIPERIDINE DERIVATIVE; TITANIUM DERIVATIVE;

EID: 0032541689     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01455-5     Document Type: Article
Times cited : (26)

References (27)
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    • [3] For recent reviews on natural products having a cis-2,6-disubstituted piperidine moiety, see: Numata A, Ibuka I. The Alkaloids, Brossi A. editor, New York, Academic Press: 1987; Vol. 31:193-315. Takahata H, Momose T. The Alkaloids, Cordell GA. editor, San Diego, Academic Press, 1993; Vol. 44:189-256. For recent syntheses of optically active cis-2,6-disubstituted piperidines, see: Munchhof MJ, Meyers AI. J. Am. Chem. Soc. 1995;117:5399-5400. Hirai Y, Watanabe J, Nozaki T, Yokoyama H, Yamaguchi S. J. Org. Chem. 1997;62:776-777. Momose T, Toyooka N, Jin M. J. Chem. Soc., Perkin Trans. 1, 1997; 2005-2013 and references cited therein.
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    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 2005-2013
    • Momose, T.1    Toyooka, N.2    Jin, M.3
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    • [4] For representative examples of natural products having a 2,6-disubstituted tetrahydropyridine moiety, see: Lotter HL, Abraham DJ, Turner CE, Knapp JE, Schiff PL, Slatkin DJ. Tetrahedron Lett. 1975; 2815-2818. Nader B, Bailey TR, Franck RW, Weinreb SM. J. Am. Chem. Soc. 1981;103:7573-7580. Colau B, Hootelé C. Can. J. Chem. 1983;61:470-472. Wasserman HH, Leadbetter MR, Kopka IE. Tetrahedron Lett. 1984;25:2391-2394. Natsume M, Ogawa M. Chem. Pharm. Bull. 1984;32:3789-3791. Bailey TR, Garigipati RS, Morton JA, Weinreb SM. J. Am. Chem. Soc. 1984;106:3240-3245. For syntheses of 2,6-disubstituted tetrahydropyridines, sec: Bonin M, Romero JR, Grierson DS, Husson HP. J. Org. Chem. 1984;49:2392-2400. Wuts PGM, Jung YW. J. Org. Chem. 1988;53:1957-1965. Comins DL, Weglarz MA. J. Org. Chem. 1991;56:2506-2512. Ahman J, Somfai P. J. Am. Chem. Soc. 1994;116:9781-9782. Huwe CM, Velder J, Blechert S. Angew. Chem., Int. Ed. Engl. 1996;35:2376-2378. Bubnov YN, Klimkina EV, Ignatenko AV, Gridnev ID. Tetrahedron Lett. 1997;38:4631-4634. Craig D, McCague R, Potter GA, Williams MRV. Synlett, 1998;55-57 and references cited therein.
    • (1975) Tetrahedron Lett. , pp. 2815-2818
    • Lotter, H.L.1    Abraham, D.J.2    Turner, C.E.3    Knapp, J.E.4    Schiff, P.L.5    Slatkin, D.J.6
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    • [4] For representative examples of natural products having a 2,6-disubstituted tetrahydropyridine moiety, see: Lotter HL, Abraham DJ, Turner CE, Knapp JE, Schiff PL, Slatkin DJ. Tetrahedron Lett. 1975; 2815-2818. Nader B, Bailey TR, Franck RW, Weinreb SM. J. Am. Chem. Soc. 1981;103:7573-7580. Colau B, Hootelé C. Can. J. Chem. 1983;61:470-472. Wasserman HH, Leadbetter MR, Kopka IE. Tetrahedron Lett. 1984;25:2391-2394. Natsume M, Ogawa M. Chem. Pharm. Bull. 1984;32:3789-3791. Bailey TR, Garigipati RS, Morton JA, Weinreb SM. J. Am. Chem. Soc. 1984;106:3240-3245. For syntheses of 2,6-disubstituted tetrahydropyridines, sec: Bonin M, Romero JR, Grierson DS, Husson HP. J. Org. Chem. 1984;49:2392-2400. Wuts PGM, Jung YW. J. Org. Chem. 1988;53:1957-1965. Comins DL, Weglarz MA. J. Org. Chem. 1991;56:2506-2512. Ahman J, Somfai P. J. Am. Chem. Soc. 1994;116:9781-9782. Huwe CM, Velder J, Blechert S. Angew. Chem., Int. Ed. Engl. 1996;35:2376-2378. Bubnov YN, Klimkina EV, Ignatenko AV, Gridnev ID. Tetrahedron Lett. 1997;38:4631-4634. Craig D, McCague R, Potter GA, Williams MRV. Synlett, 1998;55-57 and references cited therein.
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    • Nader, B.1    Bailey, T.R.2    Franck, R.W.3    Weinreb, S.M.4
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    • [4] For representative examples of natural products having a 2,6-disubstituted tetrahydropyridine moiety, see: Lotter HL, Abraham DJ, Turner CE, Knapp JE, Schiff PL, Slatkin DJ. Tetrahedron Lett. 1975; 2815-2818. Nader B, Bailey TR, Franck RW, Weinreb SM. J. Am. Chem. Soc. 1981;103:7573-7580. Colau B, Hootelé C. Can. J. Chem. 1983;61:470-472. Wasserman HH, Leadbetter MR, Kopka IE. Tetrahedron Lett. 1984;25:2391-2394. Natsume M, Ogawa M. Chem. Pharm. Bull. 1984;32:3789-3791. Bailey TR, Garigipati RS, Morton JA, Weinreb SM. J. Am. Chem. Soc. 1984;106:3240-3245. For syntheses of 2,6-disubstituted tetrahydropyridines, sec: Bonin M, Romero JR, Grierson DS, Husson HP. J. Org. Chem. 1984;49:2392-2400. Wuts PGM, Jung YW. J. Org. Chem. 1988;53:1957-1965. Comins DL, Weglarz MA. J. Org. Chem. 1991;56:2506-2512. Ahman J, Somfai P. J. Am. Chem. Soc. 1994;116:9781-9782. Huwe CM, Velder J, Blechert S. Angew. Chem., Int. Ed. Engl. 1996;35:2376-2378. Bubnov YN, Klimkina EV, Ignatenko AV, Gridnev ID. Tetrahedron Lett. 1997;38:4631-4634. Craig D, McCague R, Potter GA, Williams MRV. Synlett, 1998;55-57 and references cited therein.
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    • Wasserman, H.H.1    Leadbetter, M.R.2    Kopka, I.E.3
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    • [4] For representative examples of natural products having a 2,6-disubstituted tetrahydropyridine moiety, see: Lotter HL, Abraham DJ, Turner CE, Knapp JE, Schiff PL, Slatkin DJ. Tetrahedron Lett. 1975; 2815-2818. Nader B, Bailey TR, Franck RW, Weinreb SM. J. Am. Chem. Soc. 1981;103:7573-7580. Colau B, Hootelé C. Can. J. Chem. 1983;61:470-472. Wasserman HH, Leadbetter MR, Kopka IE. Tetrahedron Lett. 1984;25:2391-2394. Natsume M, Ogawa M. Chem. Pharm. Bull. 1984;32:3789-3791. Bailey TR, Garigipati RS, Morton JA, Weinreb SM. J. Am. Chem. Soc. 1984;106:3240-3245. For syntheses of 2,6-disubstituted tetrahydropyridines, sec: Bonin M, Romero JR, Grierson DS, Husson HP. J. Org. Chem. 1984;49:2392-2400. Wuts PGM, Jung YW. J. Org. Chem. 1988;53:1957-1965. Comins DL, Weglarz MA. J. Org. Chem. 1991;56:2506-2512. Ahman J, Somfai P. J. Am. Chem. Soc. 1994;116:9781-9782. Huwe CM, Velder J, Blechert S. Angew. Chem., Int. Ed. Engl. 1996;35:2376-2378. Bubnov YN, Klimkina EV, Ignatenko AV, Gridnev ID. Tetrahedron Lett. 1997;38:4631-4634. Craig D, McCague R, Potter GA, Williams MRV. Synlett, 1998;55-57 and references cited therein.
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    • Natsume, M.1    Ogawa, M.2
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    • [4] For representative examples of natural products having a 2,6-disubstituted tetrahydropyridine moiety, see: Lotter HL, Abraham DJ, Turner CE, Knapp JE, Schiff PL, Slatkin DJ. Tetrahedron Lett. 1975; 2815-2818. Nader B, Bailey TR, Franck RW, Weinreb SM. J. Am. Chem. Soc. 1981;103:7573-7580. Colau B, Hootelé C. Can. J. Chem. 1983;61:470-472. Wasserman HH, Leadbetter MR, Kopka IE. Tetrahedron Lett. 1984;25:2391-2394. Natsume M, Ogawa M. Chem. Pharm. Bull. 1984;32:3789-3791. Bailey TR, Garigipati RS, Morton JA, Weinreb SM. J. Am. Chem. Soc. 1984;106:3240-3245. For syntheses of 2,6-disubstituted tetrahydropyridines, sec: Bonin M, Romero JR, Grierson DS, Husson HP. J. Org. Chem. 1984;49:2392-2400. Wuts PGM, Jung YW. J. Org. Chem. 1988;53:1957-1965. Comins DL, Weglarz MA. J. Org. Chem. 1991;56:2506-2512. Ahman J, Somfai P. J. Am. Chem. Soc. 1994;116:9781-9782. Huwe CM, Velder J, Blechert S. Angew. Chem., Int. Ed. Engl. 1996;35:2376-2378. Bubnov YN, Klimkina EV, Ignatenko AV, Gridnev ID. Tetrahedron Lett. 1997;38:4631-4634. Craig D, McCague R, Potter GA, Williams MRV. Synlett, 1998;55-57 and references cited therein.
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    • (1997) Tetrahedron Lett. , vol.38 , pp. 4631-4634
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