Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2331-2334

  Araki, Shuki ^a   Horie, Tomoaki ^a   Kato, Motoshi ^a   Hirashita, Tsunehisa ^a   Yamamura, Hatsuo ^a   Kawai, Masao ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Allylation; Gallium and compounds; Indium and compounds; Michael reactions

Indexed keywords

ALKENE; GALLIUM; INDIUM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; METHYLATION; STEREOCHEMISTRY;

EID: 0033583156     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00179-3     Document Type: Article

References (19)

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2. 2. For selected examples of organogallium reagents in organic synthesis: see, (a) Araki, S.; Ito, K.; Butsugan, Y. Appl. Organomet. Chem. 1988, 2, 475-478;
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13. 3. All products gave satisfactory spectral and analytical data. 4. For 1,2-as well as 1,4-addition reactions of organoindium reagents to enones: see, Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291-296; Araki, S.; Shimizu, T.; Jin, S.-J.; Butsugan, Y. J. Chem. Soc., Chem. Commun. 1991, 824-825.
14. 3. All products gave satisfactory spectral and analytical data. 4. For 1,2-as well as 1,4-addition reactions of organoindium reagents to enones: see, Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291-296; Araki, S.; Shimizu, T.; Jin, S.-J.; Butsugan, Y. J. Chem. Soc., Chem. Commun. 1991, 824-825.
15. 5. For examples of 1,4-allylation of electron-deficient alkenes: see, Yamamoto, Y.; Nishii, S.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 386-388; Yamamoto, Y.; Nishii, S. J. Org. Chem. 1988, 53, 3597-3603.
16. 5. For examples of 1,4-allylation of electron-deficient alkenes: see, Yamamoto, Y.; Nishii, S.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 386-388; Yamamoto, Y.; Nishii, S. J. Org. Chem. 1988, 53, 3597-3603.
17. 6. Li, C. J. Tetrahedron 1996, 52, 5643-5668; Li, C. J.; Chan, T. H. "Organic Reactions in AqueousMedia", Wiley-Interscience, NY, 1977.
18. 6. Li, C. J. Tetrahedron 1996, 52, 5643-5668; Li, C. J.; Chan, T. H. "Organic Reactions in Aqueous Media", Wiley-Interscience, NY, 1977.
19. 2 gave much less 1,4-addition (< 50% yield) together with undefined products.