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Synthesis 2009(16): 2749-2755
DOI: 10.1055/s-0029-1216913
DOI: 10.1055/s-0029-1216913
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA Facile Synthesis of Two Series of Multifunctional Carbon Compounds from α,α-Dihalo Ketones Using Allylsamarium Bromide
Weitere Informationen
Received
2 March 2009
Publikationsdatum:
23. Juli 2009 (online)
Publikationsverlauf
Publikationsdatum:
23. Juli 2009 (online)

Abstract
The use of allylsamarium bromide to effect two different reactions on the common starting material, α,α-dihalo ketones, is presented. With DMF, α-halo-α-allyl aldehydes were obtained, while α-hydroxy-α-allyl aldehyde acetals were obtained in the presence of NaOMe/MeOH .
Key words
samarium - aldehydes - acetals - rearrangement - synthesis
- 1a
Yamamoto Y.Maruyama K. Heterocycles 1982, 18: 357 - 1b
Hoffmann RW. Angew. Chem., Int. Ed. Engl. 1982, 21: 555 - 1c
Yamamoto Y.Asao N. Chem. Rev. 1993, 93: 2207 - 2
Fujiwara T.Takeuchi Y. J. Fluorine Chem. 2005, 126: 941 - 3a
Takeuchi Y.Asahina M.Nagata K.Koizumi T. J. Chem. Soc. 1987, 2203 - 3b
Takeuchi Y.Murayama A.Hagi T.Koizumi T. J. Chem. Soc. Jpn., Chem. Ind. Chem. 1985, 2029 - 4
Di J.Zhang S. Synlett 2008, 1491 - 5
Aoki Y.Oshima K.Utimoto K. Synlett 1995, 1071 - 6a
Arasaki H.Iwata M.Nishimura D.Itoh A.Masaki Y. Synlett 2004, 546 - 6b
Masaki Y.Arasaki H.Iwata M. Chem. Lett. 2003, 32: 4 - 6c
Kaczmarczyk G.Jonczyk A. Synlett 1997, 921 - 6d
Stevens CL.Farkas E.Gillis B. J. Am. Chem. Soc. 1954, 76: 2695 - 6e
Teager DS.Ward HD.Murray RK. J. Org. Chem. 1993, 58: 5493 - 6f
Bacquet C.Masure D.Normant JF. J. Organomet. Chem. 1973, 50: C7 - 6g
Chandrasekhar S.Murthy T. J. Chem. Res., Synop. 1987, 414 - 6h
Aston JG.Greenburg RB. J. Am. Chem. Soc. 1940, 62: 2590 - 7
Xu X.-H.Huang R.-X.Lu R.-L.Zhang Q.-L. Chin. J. Org. Chem. 2003, 23: 865 - 8
Araki S.Shimizu T.Johar PS.Jin S.-J.Butsugan Y. J. Org. Chem. 1991, 56: 2538 - 9
Vaughan WR.Bernstein SC.Lorber ME. J. Org. Chem. 1965, 30: 1790 - 10a
Sonawane H.Bellur NS.Kulkarni DG.Ayyangar NR. Tetrahedron 1994, 50: 1243 - 10b
Silveira CC.Bernardi CR.Braga AL.Kaufman TS. Tetrahedron Lett. 2001, 42: 8947 - 10c
Park C.-H.Givens RS. J. Am. Chem. Soc. 1997, 119: 2453