Indium-catalyzed allylation of carbonyl compounds with the Mn/TMSCl system

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9245-9247

  Augé, Jacques ^a   Lubin Germain, Nadège ^a   Thiaw Woaye, Aurélie ^a  

^a UNIVERSITÉ DE CERGY PONTOISE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BROMIDE; INDIUM; KETONE; MANGANESE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION;

EID: 0033601468     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01990-5     Document Type: Article

References (18)

1. For a review, see: Cintas, P. Synthesis 1995, 1087-1096.
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6. Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747-748.
7. For applications of the aqueous Barbier-type reactions, see: (a) Chan, T. H.; Li, C. J. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
8. (b) Lubineau, A.; Augé, J. Topics in Current Chemistry 1999, 206, 1-39.
9. Araki, S.; Jin, S.-J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736-1738.
10. Miyai, T.; Inoue, K.; Yasuda, M.; Baba, A. Synlett 1997, 699-700.
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12. Augé, J.; Gil, R.; Kalsey, S. Tetrahedron Lett. 1999, 40, 67-70.
13. Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172-177.
14. Manganese must be highly activated in order to promote similar allylation reactions, see: Cahiez, G.; Chavant, P.-Y. Tetrahedron Lett. 1989, 30, 7373-7376. Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012.
15. Manganese must be highly activated in order to promote similar allylation reactions, see: Cahiez, G.; Chavant, P.-Y. Tetrahedron Lett. 1989, 30, 7373-7376. Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012.
16. Typical procedure: Indium (0.2 mmol) and manganese (10 mmol) powder were placed in a Schlenk tube. After stirring the mixture for 15 min were added successively THF (12.5 ml), allyl bromide (5 mmol), benzaldehyde (2 mmol), TMSCl (10 mmol). The black heterogeneous mixture, turning grey then white, was allowed to react for 3 h under a vigorous stirring. Water (12 ml) was then added dropwise and the adduct was extracted with ethyl acetate. The organic layers were dried, filtered off and then evaporated. A flash chromatography yielded 1-phenyl-but-3-en-1-ol (86%) as a pure compound.
17. Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931-1937.
18. 13C NMR spectroscopy. NMR spectra of syn adducts were previously published, see: Hallett, D. J.; Thomas, E. J. Synlett 1994, 87-88.