Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(9): 1375-1380
DOI: 10.1055/s-2004-822399
DOI: 10.1055/s-2004-822399
PAPER
© Georg Thieme Verlag Stuttgart · New YorkIron(III) Chloride Catalysis of the Acetal-Ene Reaction
Further Information
Received
3 May 2004
Publication Date:
08 June 2004 (online)
Publication History
Publication Date:
08 June 2004 (online)

Abstract
Iron(III) chloride was found to act as a very efficient catalyst in the acetal-ene reaction involving 1,1-disubstituted alkenes.
Key words
ene reaction - acetals - catalysis - iron - Lewis acids
- 1
Mukaiyama T.Hayashi M. Chem. Lett. 1974, 15 - Reviews:
- 2a
Fleming I. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I. Pergamon; London: 1991. p.563 - 2b
Chan T.-H. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I. Pergamon; London: 1991. p.595 - 2c
Carreira EM. In Comprehensive Asymmetric Catalysis Vol. III:Jacobsen EN.Pfaltz A.Yamamoto H. Springer Verlag; Berlin: 1999. p.997 - Reviews:
- 3a
Snider BB. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I. Pergamon; London: 1991. p.527 - 3b
Berrisford DJ.Bolm C. Angew. Chem., Int. Ed. Engl. 1995, 34: 1717 - 3c
Mikami K.Terada M. In Comprehensive Asymmetric Catalysis Vol. III:Jacobsen EM.Pfaltz A.Yamamoto H. Springer Verlag; Berlin: 1999. p.1143 - 3d
Mikami K.Takeshi N. In Catalytic Asymmetric Synthesis 2nd ed.:Iwao O. Wiley-VCH; New York: 1999. p.543 - 4a
Johnson WS.Kinnel RB. J. Am. Chem. Soc. 1966, 88: 3861 - 4b
Bunnelle WH.Seamon DW.Mohler DL.Ball TF.Thompson DW. Tetrahedron Lett. 1984, 25: 2653 - 4c
Melany ML.Lock GA.Thompson DW. J. Org. Chem. 1985, 50: 3925 - 4d
Overman LE.Castañeda A.Blumenkopf TA. J. Am. Chem. Soc. 1986, 108: 1303 - 4e
Overman LE.Thompson AS. J. Am. Chem. Soc. 1988, 110: 2248 - 4f
Castañeda A.Kucera DJ.Overman LE. J. Org. Chem. 1989, 54: 5695 - 4g
Blumenkopf TA.Matthias B.Castañeda A.Look GC.Overman LE.Rodriguez D.Thompson SA. J. Am. Chem. Soc. 1990, 112: 4386 - 4h
Blumenkopf TA.Look GC.Overman LE. J. Am. Chem. Soc. 1990, 112: 4399 - 4i
Berger D.Overman LE. Synlett 1992, 811 - 4j
Berger D.Overman LE.Renhowe PA. J. Am. Chem. Soc. 1993, 115: 9305 - 4k
Berger D.Overman LE.Renhowe PA. J. Am. Chem. Soc. 1997, 119: 2446 - 4l
Muratake H.Natsume M. Tetrahedron Lett. 2002, 43: 2913 - 5a
Paul R.Tchelitcheff S. Bull. Soc. Chim. Fr. 1951, 125 - 5b
Snider BB.Burbaum BW. Synth. Comm. 1986, 16: 1451 - 5c
Mayr H.Brügen U. Chem. Ber. 1988, 339 - 6
Mukaiyama T.Wariishi K.Furuya M.Kobayashi S. Chem. Lett. 1989, 1277 - 7a
Ishihara K.Nakamura H.Yamamoto H. Synlett 2000, 1245 - 7b
Nakamura H.Ishihara K.Yamamoto H. J. Org. Chem. 2002, 67: 5124 - Iron(III) chloride is also an effective catalyst for the reaction of aldehydes and acetals with allylsilanes:
- 8a
Watahiki T.Oriyama T. Tetrahedron Lett. 2002, 43: 8959 - 8b
Watahiki T.Akabane Y.Mori S.Oriyama T. Org. Lett. 2003, 5: 3045 - 9a
Denmark SE.Willson TM. J. Am. Chem. Soc. 1989, 111: 3475 - 9b
Denmark SE.Almstead NG. J. Org. Chem. 1991, 56: 6458 - 9c
Denmark SE.Almstead NG. J. Am. Chem. Soc. 1991, 113: 8089 - 9d
Sammakia T.Smith RS. J. Am. Chem. Soc. 1994, 116: 7915 - 9e
Sammakia T.Smith RS. J. Am. Chem. Soc. 1994, 114: 10998 - 9f
Linderman RJ.Chen K. J. Org. Chem. 1996, 61: 2441 - 10
Hayushi M.Masaji I.Inubushi A.Mukaiyama T. Bull. Chem. Soc. Jpn. 1988, 61: 4037 - 11
Rose PDR.Williams A. J. Chem. Soc., Perkin Trans. 2 2002, 1589