Indium-mediated allylation of the N,N-dimethyl glyoxal mono-hydrazone: One-pot synthesis of bis-homoallyl, and of homoallyl-alkyl 1,2-diols

Synlett

Volumn , Issue 10, 1999, Pages 1585-1587

  Cerè, Vanda ^a   Peri, Francesca ^a   Pollicino, Salvatore ^a   Ricci, Alfredo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Alkylation; Allylation; Glyoxal; Hydrazone; Indium

Indexed keywords

ALLYL COMPOUND; GLYOXAL DERIVATIVE; HYDRAZONE DERIVATIVE; INDIUM;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0032872536     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2881     Document Type: Article

References (15)

1. (a) Yamamoto, Y.; Maruyama, K. Heterocycles 1982, 18, 357.
2. (b) Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1982, 21, 555.
3. (c) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243.
4. (d) Yamamoto, Y. Aldrichim. Acta 1987, 20, 45.
5. Paquette, L.A.; Mitzel, T.M. J. Am. Chem. Soc. 1996, 118, 1931 and references cited therein.
6. Cerè, V.; Peri, F.; Pollicino, S.; Ricci, A. Tetrahedron 1999, 55, 1087.
7. Severin, T.; Phoelmann, H.H. Chem. Ber. 1977, 7, 1269.
8. The following conditions are usually reported in the literature for the allylation of carbonyl and imino derivatives: C=X/ AllylX/In: 1/2/1.
9. Volkman, R.A. In "Comprehensive Organic Synthesis" Trost, B.M.; Fleming, I. Ed.; Pergamon Press: New York 1991, Vol.1, p. 355.
10. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138, and references therein.
11. (a) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. I. Can. J. Chem. 1994, 72, 1181.
12. (b) Bernardelli, P.; Paquette, L.A. J. Org. Chem. 1997, 62, 8284.
13. The intermediacy of an allyl indium species in the In-mediated allylation of aldehydes has been recently proposed: Isaac, M.B.; Chan, T.H. Tetrahedron Lett. 1995, 49, 8957.
14. Compounds 4a-c could be isolated and subjected to allylation under the same conditions used in the one-pot two-step reaction without any sizeable variation of the chemical yields and of the stereochemical outcome.
15. 2: C, 68.50;