A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3189-3192

  Tokuyama, Hidetoshi ^a   Yokoshima, Satoshi ^a   Yamashita, Tohru ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOKETONE; AMINOTHIOL; KETONE; PALLADIUM; THIOESTER;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0032516391     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00456-0     Document Type: Article

References (31)

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2. (b) Jorgenson, M. J. Org. React. 1970, 18, 1.
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13. 2 catalyzed ketone formation from S-(2-pyridyl) thioates in the presence of Zn and alkyl iodide: Onaka, M.; Matsuoka, Y.; Mukaiyama, T. Chem. Lett. 1981, 531.
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15. (b) Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L. Tetrahedron Lett. 1987, 28, 2053.
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18. 3, in toluene-water) gave the desired aryl ketone in low yield.
19. 3CN, the reaction proceeded considerably slowly in THF and benzene. The reaction in DMF did not proceed at all.
20. 12. (a) For a general review of preparation of organozinc reagents, see: Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117, and references cited therein.
21. (b) Bouhlel, E.; Rathke, M. W. Syn. Commun. 1991, 21, 133.
22. (c) β-Phenethylzinc iodide; Grondin, J.; Hajjad, F.; Vottero, P.; Blancou, H.; Commeyras, A. C. R. Acad. Sci. Paris, t, 307, Ser II 1988, 1699.
23. (d) Benzylzinc iodide; Berk, S. C.; Knochel, P.; Yeh, M. C. P. J. Org. Chem. 1988, 53, 5791.
24. (e) Phenylzinc iodide; Majid, T. N.; Knochel, P. Tetrahedron Lett. 1990, 31, 4413.
25. 13. Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. -I. Org. Synth. Coll. Vol 8 1993, 274.
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27. 15. HPLC analyses were performed with a chiral HPLC column using a racemic mixture as references (DAICEL Chiralcel-OJ, 4.6 mm I.D. × 250 mm, 90/10 n-hexane/2-propanol, 1.0 mL/min, 40 °C).
28. 16. HPLC analysis was performed with a chiral HPLC column using a racemic mixture as references (DAICEL Chiralcel-OD, 4.6 mm I.D. × 250 mm, 95/5 n-hexane/2-propanol, 1.0 mL/min, 40 °C).
29. 17. The thiol ester was prepared from N-Cbz-L-phenylalanine via mixed anhydride; see ref. 9a.
30. 18. EtZnI was prepared by heating activated zinc powder (3.1 g, activated according to ref. 14) and ethyl iodide (1.93 mL) in refluxing THF (24 mL) for 2 hours. The concentration of the reagent was estimated by titration to be 0.90 M.
31. 3: C, 72.99; H, 6.79; N, 4.44. Found: C, 73.29; H, 6.80; N, 4.50.