Divergent reaction pathways in amine additions to β-lactone electrophiles. An application to β-peptide synthesis

Tetrahedron

Volumn 58, Issue 35, 2002, Pages 7081-7091

  Nelson, Scott G ^a   Spencer, Keith L ^a   Cheung, Wing S ^a   Mamie, Steven J ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Amino acids; Asymmetric catalysis; Lactones; Nucleophilic additions; Peptides

Indexed keywords

ALDEHYDE DERIVATIVE; AMIDE; AMINE; AMINO ACID DERIVATIVE; ANION; AZIDE; BETA AMINO ACID; HALIDE; LACTONE DERIVATIVE; NITROGEN; PEPTIDE DERIVATIVE; SULFONAMIDE;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHIRAL CHROMATOGRAPHY; CYCLOADDITION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; PEPTIDE SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037178970     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00722-6     Document Type: Article

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18. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
19. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
20. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
21. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
22. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
23. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
24. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
25. Assymetric β-amino acid synthesis employing optically active starting materials or chiral auxiliaries: (a) Ref. 15. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cole, D. C. Tetrahedron 1994, 50, 9517. (d) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117. See also: (e) Enders, D.; Bettray, W.; Raabe, G.; Runsink, J. Synthesis 1994, 1322. (f) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455-457. (g) Podlech, J.; Seebach, D.; Liebigs Ann. 1995, 1217. (h) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121. and references therein. (i) Farras, J.; Ginesta, X.; Sutton, P.W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
26. Recent catalytic asymmetric synthesis of β-amino acid derivatives: (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1. 1996, 2823 (b) Kobayashi, S., Ishitani, H., Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Sibi, M.P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (d) Zhou, F.; Detty, M. R.; Lachicotte, R. J. Tetrahedron Lett. 1999, 40, 585. (e) Meyers, J.K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (f) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
27. Recent catalytic asymmetric synthesis of β-amino acid derivatives: (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1. 1996, 2823 (b) Kobayashi, S., Ishitani, H., Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Sibi, M.P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (d) Zhou, F.; Detty, M. R.; Lachicotte, R. J. Tetrahedron Lett. 1999, 40, 585. (e) Meyers, J.K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (f) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
28. Recent catalytic asymmetric synthesis of β-amino acid derivatives: (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1. 1996, 2823 (b) Kobayashi, S., Ishitani, H., Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Sibi, M.P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (d) Zhou, F.; Detty, M. R.; Lachicotte, R. J. Tetrahedron Lett. 1999, 40, 585. (e) Meyers, J.K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (f) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
29. Recent catalytic asymmetric synthesis of β-amino acid derivatives: (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1. 1996, 2823 (b) Kobayashi, S., Ishitani, H., Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Sibi, M.P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (d) Zhou, F.; Detty, M. R.; Lachicotte, R. J. Tetrahedron Lett. 1999, 40, 585. (e) Meyers, J.K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (f) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
30. Recent catalytic asymmetric synthesis of β-amino acid derivatives: (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1. 1996, 2823 (b) Kobayashi, S., Ishitani, H., Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Sibi, M.P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (d) Zhou, F.; Detty, M. R.; Lachicotte, R. J. Tetrahedron Lett. 1999, 40, 585. (e) Meyers, J.K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (f) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
31. Recent catalytic asymmetric synthesis of β-amino acid derivatives: (a) Falborg, L.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1. 1996, 2823 (b) Kobayashi, S., Ishitani, H., Ueno, M. J. Am. Chem. Soc. 1998, 120, 431. (c) Sibi, M.P.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615. (d) Zhou, F.; Detty, M. R.; Lachicotte, R. J. Tetrahedron Lett. 1999, 40, 585. (e) Meyers, J.K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (f) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
32. (a) Arnold L.D., Kalantar T.H., Vederas J.C. J. Am. Chem. Soc. 107:1985;7105 (b) Griesbeck A., Seebach D. Helv. Chim. Acta. 70:1987;1326 (c) Arnold L.D., May R.G., Vederas J.C. J. Am. Chem. Soc. 110:1988;2237 (d) Castagnani R., De Angelis F., De Fusco E., Giannessi F., Misiti D., Meloni D., Tinti M.O. J. Org. Chem. 60:1995;8318 (e) Bernabei I., Castagnani R., De Angelis F., De Fusco E., Giannessi F., Misiti D., Muck S., Scafetta N., Tinti M.O. Chem. Eur. J. 2:1996;826.
33. . For an alternative approach to β-amino acid derivatives derived from β-lactones, see: Yang H.W., Romo D. J. Org. Chem. 64:1999;7657.
34. . For recent developments in asymmetric β-lactone synthesis, see: Yang H.W., Romo D. Tetrahedron. 55:1999;6403.
35. . β-Lactones possessing α-branched substituents are not obtained in sufficiently high enantioselectivities from the catalyzed AAC reactions to be generally useful. Lactone 1g was readily prepared from the enzyme-mediated resolution of the racemic β-lactone derived from the achiral AAC reaction, see: (a) Nelson S.G., Spencer K.L. J. Org. Chem. 65:2000;1227 (b) Koichi Y., Suginaka K., Yamamoto Y. J. Chem. Soc., Perkin Trans. 1. 1995;1645.
36. To verify that lactone ring opening was proceeding with rigorous inversion of stereochemistry, the enantiomeric purities of azides 11a-c were determined by chiral HPLC (Chiralcel OD-H column) of the methyl esters derived from 11a and 11b, and the benzyl ester derived from 11c. See Section 6 for full procedural details.
37. . (a) Compounds 12b and 12d: Alcón M., Canas M., Poch M., Moyano A., Pericás M.A., Riera A. Tetrahedron Lett. 35:1994;1589. (b) Compound 12c: Gordon E.M., Godfrey J.D., Delaney N.G., Asaad M.M., Von Langen D., Cushman D.W. J. Med. Chem. 31:1988;2199. (c) Compound 12e: Mendre C., Rodriguez M., Laur J., Aumelas A., Martinez J. Tetrahedron. 44:1988;4415.
38. For the synthesis of β-lactones via lactonization of β-hydroxy carboxylate derivatives, see Ref. 21 and references therein.
39. . Acidic work-up of the dimethylsulfoxide reaction solutions should remove any remaining azide reagent by conversion to the sulfoximine, see: Johnson C.R., Rogers P.E. J. Org. Chem. 38:1973;1793.
40. The potassium and magnesium halide carbamate salts were unstable toward decomposition during the course of the reaction.
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