Direct synthesis of dithioketals from N,N-dialkylhydrazones

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7955-7958

  Díez, Elena ^a   López, Ana M ^a   Pareja, Carmen ^a   Martín, Eloísa ^a   Fernández, Rosario ^a   Lassaletta, José M ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; HYDRAZONE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032558659     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01728-6     Document Type: Article

References (26)

1. 1. Enders, D. In Asymmetric Synthesis; Morrison, J.D., Ed.; Academic Press: Orlando, 1984; Vol 3, Chapter 4, pp 275-339.
2. 2. Selected recent examples: (a) Nakamura, E.; Kubota, K.; Sakata, G. J. Am. Chem. Soc. 1997, 119, 5457-5458.
3. (b) Sturino, C.F.; Fallis, A.G. J. Am. Chem. Soc. 1994, 116, 7447-7448.
4. (c) Mino, T.; Yamashita, M. J. Org. Chem. 1996, 61, 1159-1160.
5. (d) Maruoka, K.; Oishi M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 2289-2290.
6. 3. (a) Lassaletta, J.M.; Fernández, R. Tetrahedron Lett. 1992, 33, 3691-3694.
7. (b) Lassaletta, J.M.; Fernández, R.; Gasch, C.; Vázquez, J. Tetrahedron 1996, 52, 9143-9160.
8. (c) Fernández, R.; Gasch, C.; Lassaletta, J.M.; Llera, J.M. Synthesis 1996, 627-632.
9. (d) Enders, D.; Syrig, R.; Raabe, G.; Fernández, R.; Gasch, C.; Lassaletta, J.M.; Liera, J.M. Synthesis 1996, 48-52.
10. (e) Lassaletta, J.M.; Fernández, R.; Martín-Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002-7003.
11. (f) Díez, E.; Fernández, R.; Gasch, C.; Lassaletta, J.M.; Llera, J.M.; Martín-Zamora, E.; Vázquez, J. J. Org. Chem. 1997, 62, 5144-5155.
12. 4. Lassaletta, J.M.; Fernández, R.; Martín-Zamora, E.; Pareja, C. Tetrahedron Lett. 1996, 37, 5787-5790.
13. 5. For a recent, comprehensive review on the asymmetric addition of organometallics to the CN double bond of hydrazones see: Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1846.
14. 6. Fernández, R.; Gasch, C.; Lassaletta, J.M.; Llera, J.M.; Vázquez, J. Tetrahedron Lett. 1993, 34, 141-144.
15. 7. With the exception of formaldehyde derivatives, the aza-enamine-like, nucleophilic reactivity of dialkylhydrazones is limited to the reactions with highly electrophilic compounds: (a) Brehme, R. Chem. Ber. 1990, 123, 2039-2046.
16. (b) Brehme, R.; Nikolajewski, H.E. Tetrahedron Lett. 1982, 23, 1131-1134.
17. (c) Brehme, R.; Nikolajewski, H.E. Tetrahedron 1976, 32, 731-736.
18. (d) Kamitori, Y.; Hojo, M.; Masuda, R.; Fujitani, T.; Ohara, S.; Yokohama, T. J. Org. Chem. 1988, 53, 129-135.
19. (e) Kamitori, Y.; Hojo, M.; Masuda, R.; Yoshida, T.; Ohara, S.; Yamada, K.; Yoshikawa, N. J. Org. Chem. 1988, 53, 519-526.
20. 8. Ager, D.J.; In Umpoled Synthons: A Survey of Sources and Uses in Synthesis; Hase, T.A.; Ed.: Wiley: New York, 1987, Chapter 2, pp. 19-72.
21. 9. Oyamada, H.; Kobayashi, S. Synlett 1998, 249-250.
22. 2 (15 mL) and treated with p-TsOH (1.1 mmol). Work-up was performed as described above.
23. 11. Hydrazones 1g-i were synthesized as previously described before: see Ref. 3f.
24. 12. No 1,4-addition by-products were detected in the reaction mixture.
25. 13. The corresponding free aldehyde resulting from ozonolysis of the same starting hydrazone proved to be extremely prone to racemization: See Ref. 3e.
26. 14. For a review on the use of formaldehyde SAMP hydrazone as chiral, neutral formylating reagent see: Enders, D.; Bolkenius, M.; Vázquez, J.; Lassaletta, J.M.; Fernández, R. J. prakt. Chem. 1998, 340, 281-285. This compound can be purchased from Merck-Schuchardt.