Rhodium-catalyzed carbonyl allylations by allylic alcohols with tin(II) chloride

Tetrahedron Letters

Volumn 45, Issue 49, 2004, Pages 8969-8971

  Masuyama, Yoshiro ^a   Kaneko, Yusuke ^a   Kurusu, Yasuhiko ^a  

^a SOPHIA UNIVERSITY   (Japan)

Author keywords

Allylrhodium; Carbonyl allylation; Nucleophilic addition; Tin(II) chloride

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; CARBONYL DERIVATIVE; RHODIUM;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

GADUS MORHUA;

EID: 8644248155     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.051     Document Type: Article

References (24)

1. For reviews containing carbonyl allylations by allylic alcohols via umpolung of π-allylpalladium, see: Y. Masuyama J. Synth. Org. Chem. Jpn. 50 1992 202
2. Y. Masuyama L.S. Liebeskind Advances in Metal-Organic Chemistry Vol. 3 1994 JAI Press Greenwich, CT 255
3. Y. Tamaru J. Tsuji Perspectives in Organopalladium Chemistry for the XXI Century 1999 Elsevier Science Switzerland 215
4. Y. Tamaru E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis 2002 Wiley New York 1917
5. J.P. Takahara, Y. Masuyama, and Y. Kurusu J. Am. Chem. Soc. 114 1992 2577
6. M. Kimura, T. Tomizawa, Y. Horino, S. Tanaka, and Y. Tamaru Tetrahedron Lett. 41 2000 3627
7. S. Araki, T. Kamei, T. Hirashita, H. Yamamura, and M. Kawai Org. Lett. 2 2000 847
8. T. Hirashita, S. Kambe, and S. Araki Abstracts of 50th Symposium on Organometallic Chemistry, Osaka, Japan 2003 Kinki Chemical Society Japan B103
9. For reactions of π-allylrhodium complexes derived from allylic halides, tosylates, and carbonates, see: J.F. Nixon, J.S. Poland, and B. Wilkins J. Organomet. Chem. 92 1975 393
10. A.E. Crease, B. Das Gupta, M.D. Johnson, and S. Moorhouse J. Chem. Soc., Dalton Trans. 1978 1821
11. M.D. Fryzuk Inorg. Chem. 21 1982 2134
12. R.A. Periana, and R.G. Bergman J. Am. Chem. Soc. 108 1986 7346
13. E.B. Tjaden, and J.M. Stryker J. Am. Chem. Soc. 112 1990 6420
14. C.S. Chin, S.Y. Shin, and C. Lee J. Chem. Soc., Dalton Trans. 1992 1323
15. T. Muraoka, I. Matsuda, and K. Itoh J. Am. Chem. Soc. 122 2000 9552
16. N. Tsukada, T. Sato, and Y. Inoue Chem. Commun. 2001 237
17. For rhodium-catalyzed enantioselective allylation of arylaldehydes with allylstannane, see: M. Shi, G.-X. Lei, and Y. Masaki Tetrahedron: Asymmetry 10 1999 2071
18. For water-promoted rhodium-catalyzed reactions, see: T. Hayashi, M. Takahashi, Y. Takaya, and M. Ogasawara J. Am. Chem. Soc. 124 2002 5052
19. S. Oi, Y. Honma, and Y. Inoue Org. Lett. 4 2002 667 and references cited therein
20. The reaction in refluxing THF produced a mixture of nonpolar olefinic compounds of which no structures were determined by instrumental analyses
21. 1H NMR) with those of authentic samples. See: (a) Ref. 2
22. A. Ito, M. Kishida, Y. Kurusu, and Y. Masuyama J. Org. Chem. 65 2000 494
23. 2 was unsuccessful in detecting an allylrhodium complex; at 25°C 2-propenol (1) remained intact, while at 50°C no structure of products other than propene was confirmed. For nucleophilic addition of σ-allylpalladium complexes to aldehydes, see: H. Nakamura, H. Iwama, and Y. Yamamoto J. Am. Chem. Soc. 118 1996 6641
24. 2O (0.1 mL), 50°C, 48 h, y 41%, α/γ = 34/66