Asymmetric synthesis of tetronic acids by Blaise reaction of protected optically active cyanohydrins

Tetrahedron Asymmetry

Volumn 7, Issue 3, 1996, Pages 663-666

  Duffield, Jonathan J ^a   Regan, Andrew C ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

TETRONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0029915188     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00059-6     Document Type: Article

References (23)

1. For recent reviews on the synthesis and reactions of optically active cyanohydrins, see: North, M. Synlett, 1993, 807-820; Effenberger, F. Angew. Chem., Int. Ed. Engl., 1994, 33, 1555-1564.
2. For recent reviews on the synthesis and reactions of optically active cyanohydrins, see: North, M. Synlett, 1993, 807-820; Effenberger, F. Angew. Chem., Int. Ed. Engl., 1994, 33, 1555-1564.
3. Effenberger, F; Ziegler, T.; Förster, S. Angew. Chem., Int. Ed. Engl., 1987, 26, 458-460.
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5. Krepski, L.R.; Jensen, K.M.; Heilmann, S.M. Synthesis, 1986, 301-3; Brussee, J.; Dofferhoff, F.; Kruse, C.G.; van der Gen, A. Tetrahedron, 1990, 46, 1653-1658.
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10. Haynes, L.J.; Plimmer, J.R. Q. Rev. Chem. Soc., 1960, 14, 292-315.; Pattenden, G. Fortschr. Chem. Org. Naturst., 1978, 35, 133-198.
11. For examples of previous syntheses of optically active tetronic acids, see the following, and references contained therein: Desmaële, D. Tetrahedron, 1992, 48, 2925-2934; Wrobel, J.E.; Ganem, B. J. Org. Chem., 1983, 48, 3761-3764; Boll, P.M.; Sorenson, E.; Balieu, E. Acta. Chem. Scand., 1968, 22, 3251-3255; Witiak, D.T.; Tehin, A.K. J. Org. Chem., 1990, 55, 1112-1114; Brandänge, S; Flodman, L.; Norberg, Å. J. Org. Chem., 1984, 49, 927-928.
12. For examples of previous syntheses of optically active tetronic acids, see the following, and references contained therein: Desmaële, D. Tetrahedron, 1992, 48, 2925-2934; Wrobel, J.E.; Ganem, B. J. Org. Chem., 1983, 48, 3761-3764; Boll, P.M.; Sorenson, E.; Balieu, E. Acta. Chem. Scand., 1968, 22, 3251-3255; Witiak, D.T.; Tehin, A.K. J. Org. Chem., 1990, 55, 1112-1114; Brandänge, S; Flodman, L.; Norberg, Å. J. Org. Chem., 1984, 49, 927-928.
13. For examples of previous syntheses of optically active tetronic acids, see the following, and references contained therein: Desmaële, D. Tetrahedron, 1992, 48, 2925-2934; Wrobel, J.E.; Ganem, B. J. Org. Chem., 1983, 48, 3761-3764; Boll, P.M.; Sorenson, E.; Balieu, E. Acta. Chem. Scand., 1968, 22, 3251-3255; Witiak, D.T.; Tehin, A.K. J. Org. Chem., 1990, 55, 1112-1114; Brandänge, S; Flodman, L.; Norberg, Å. J. Org. Chem., 1984, 49, 927-928.
14. For examples of previous syntheses of optically active tetronic acids, see the following, and references contained therein: Desmaële, D. Tetrahedron, 1992, 48, 2925-2934; Wrobel, J.E.; Ganem, B. J. Org. Chem., 1983, 48, 3761-3764; Boll, P.M.; Sorenson, E.; Balieu, E. Acta. Chem. Scand., 1968, 22, 3251-3255; Witiak, D.T.; Tehin, A.K. J. Org. Chem., 1990, 55, 1112-1114; Brandänge, S; Flodman, L.; Norberg, Å. J. Org. Chem., 1984, 49, 927-928.
15. For examples of previous syntheses of optically active tetronic acids, see the following, and references contained therein: Desmaële, D. Tetrahedron, 1992, 48, 2925-2934; Wrobel, J.E.; Ganem, B. J. Org. Chem., 1983, 48, 3761-3764; Boll, P.M.; Sorenson, E.; Balieu, E. Acta. Chem. Scand., 1968, 22, 3251-3255; Witiak, D.T.; Tehin, A.K. J. Org. Chem., 1990, 55, 1112-1114; Brandänge, S; Flodman, L.; Norberg, Å. J. Org. Chem., 1984, 49, 927-928.
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17. Zandbergen, P.; van der Linden, J.; Brussee J.; van der Gen, A. Synth. Commun., 1991, 21, 1387-1391.
18. Obtained from Sigma Chemical, catalogue number A3265.
19. Shelled almonds were purchased from a local edible nut store, and were ground in a pestle and mortar and defatted three times under ethyl acetate.
20. Satisfactory spectroscopic data and accurate mass measurements were obtained for all new compounds.
21. Dale, J.A.; Dull, D.L.; Mosher, H.S. J. Org. Chem., 1969, 34, 2543-2549.
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