Preparation of functionalized zinc borates and their coupling reaction with allylic acetates

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7537-7540

  Kobayashi, Yuichi ^a   Tokoro, Yuko ^a   Watatani, Kengo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Allylation; Boron and compounds; Coupling reactions; Zinc and compounds

Indexed keywords

ACETIC ACID; BORON DERIVATIVE; FUNCTIONAL GROUP; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032497711     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01639-6     Document Type: Article

References (13)

1. 1. See ref. 6-10 of the preceding paper.
2. 2b This result indicates that the present reaction proceeds with the widely accepted mechanism for the hard nucleophiles and involves formation of the π-allylnickel inter-mediates followed by the transmetalation with the zinc borates and the subsequent reductive elimination. (a) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730-4743.
3. (b) Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833-4840. (equation presented)
4. 3. See ref. 16 of the preceding paper.
5. 4. Earlier attempt of this type of reaction: see ref. 12 of the preceding paper.
6. 5. Brown, H. C.; Cole, T. E. Organometal. 1983, 2, 1316-1319.
7. 6. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
8. 7. Difference in the reaction site between MeZnCl and the phosphonate anions (boron atom vs aldehyde carbon) is understandable on the basis of the thermodynamic (for anion derived from the phosphonates) and kinetic (for MeZnCl) nature of the reactions. Substitution reaction of compounds which possess a sterically hindered and thence more stable pinacol boronate ester-group is reported in ref. 8.
9. 8. Kamabuchi, A.; Moriya, T.; Miyaura, N.; Suzuki, A. Synth. Commun. 1993, 23, 2851-2859.
10. 9. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-4371.
11. 10. Tucker, C. E.; Davidson, J.; Knochel, P. J. Org. Chem. 1992, 57, 3482-3485.
12. 11. Unpublished result.
13. 12. This paper is dedicated to Professor Sigeru Torii in commemoration of his retirement from Okayama University.