Allylic tin(IV)-tin(II) chloride-acetonitrile as a novel system for allylation of carbonyls or imines

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5951-5954

  Yasuda, Makoto ^a   Sugawa, Yoshihiro ^a   Yamamoto, Akihiro ^a   Shibata, Ikuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALDEHYDE; CARBONYL DERIVATIVE; CINNAMALDEHYDE; IMINE; KETONE; TIN; TIN CHLORIDE; TIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030581333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01285-3     Document Type: Article

References (15)

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2. 2. (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis, Butterworth, London, 1987.
3. (b) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395-7426.
4. 3. Yano, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1992, 65, 66-70.
5. 3 has been reported to show the stereoselective allylation toward carbonyls: (a) Keck, G. E.; Abbott, D. E. Tetrahedron Lett. 1984, 25, 1883-1886.
6. (b) Keck, G. E.; Abbott, D. E.; Borden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927-3930.
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9. 5. (a) Lickiss, P. D. Chemistry of Tin; Harrison, P. G., Ed.; Blackie: Glasgow and London, 1989; Chapter 7.
10. (b) Neumann, W. P. Chem. Rev. 1991, 91, 311-334, and references cited therein.
11. 6. Monomeric dicoordinate dialkylstannylene which is stabilized by bulky substituents has been synthesized and characterized: Kira, M.; Yauchibara, R.; Hirano, R.; Kabuto, C.; Sakurai H. J. Am. Chem. Soc. 1991, 113, 7785-7787.
12. 7. (a) Yamamoto, Y. Acc. Chem. Res. 1987, 20, 243-249.
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15. (d) Keck, G. E.; Savin, K. A.; Cressman, E. N. K. Abbott, D. E. J. Org. Chem. 1994, 59, 7889-7896.