RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2006(24): 4252-4256
DOI: 10.1055/s-2006-950350
DOI: 10.1055/s-2006-950350
PAPER
© Georg Thieme Verlag Stuttgart · New York
Efficient Trimethylsilylation and Tetrahydropyranylation of Alcohols in the Presence of 1,3-Dibromo-5,5-dimethylhydantoin
Weitere Informationen
Received
31 July 2006
Publikationsdatum:
02. November 2006 (online)
Publikationsverlauf
Publikationsdatum:
02. November 2006 (online)
Abstract
Chemoselective trimethylsilylation and tetrahydropyranylation of benzylic and primary and secondary aliphatic alcohols proceed efficiently in the presence of 1,3-dibromo-5,5-dimethylhydantoin (DBH) under mild and completely heterogeneous reaction conditions in excellent yields.
Key words
alcohols - 1,3-dibromo-5,5-dimethylhydantoin - trimethylsilylation - tetrahydropyranylation - heterogeneous reaction conditions
-
1a
Pinnick WH.Bal BS.Lajis NH. Tetrahedron Lett. 1978, 4261 -
1b
Morita T.Okomoto Y.Sakuti H. Tetrahedron Lett. 1980, 21: 835 -
1c
Olah G.Husain H.Gupta BGB.Salem GF.Narang SD. J. Org. Chem. 1981, 46: 5212 -
1d
Amantini D.Fringuelli F.Pizzo P.Vaccaro L. J. Org. Chem. 2001, 66: 6743 -
2a
Cossy J.Pale P. Tetrahedron Lett. 1978, 6093 -
2b
Tarkelson S.Anisworth C. Synthesis 1976, 722 - 3
Bruynes CA.Jurrines TK. J. Org. Chem. 1982, 47: 3966 -
4a
Zhang ZH.Li TS.Yang F.Fu CG. Synth. Commun. 1998, 28: 305 -
4b
Curini M.Epifano F.Marcotullio MC.Rosati O.Constantino U. Synth. Commun. 1999, 29: 541 -
4c
Firouzabadi H.Iranpoor N.Amani K.Nowrouzi F. J. Chem. Soc., Perkin Trans. 1 2002, 2601 -
4d
Karimi B.Golshani B. J. Org. Chem. 2000, 65: 7228 -
4e
Khazaei A.Zolfigol MA.Rostami A.Ghorbani CA. Catal. Commun. 2006, in press -
4f
Shirini F.Zolfigol MA.Mohammadi K. Phosphorous, Sulfur Silicon Relat. Elem. 2003, 178: 1567 -
4g
Shirini F.Zolfigol MA.Abedini M. Bull. Chem. Soc. Jpn. 2005, 78: 1982 -
5a
Jones RG.Mann MJ. J. Am. Chem. Soc. 1953, 75: 4048 -
5b
Miyashita M.Yoshikoshi A.Grieco PA. J. Org. Chem. 1977, 42: 3772 -
6a
Ogawa Y.Shibasaki M. Tetrahedron Lett. 1984, 25: 663 -
6b
Namboodiri VV.Varma RS. Tetrahedron Lett. 2002, 43: 1143 - 7
Ravindranath N.Ramesh C.Das B. Synlett 2001, 1777 - 8
Rezai N.Meybodi FA.Salehi P. Synth. Commun. 2000, 30: 1799 - 9
Karimi B.Khalkhali M. J. Mol. Catal. A: Chem. 2005, 232: 113 - 10
Karimi B.Maleki J. Tetrahedron Lett. 2002, 43: 5353 - 11
Keh CCK.Namboodiri VV.Varma RS.Li CJ. Tetrahedron Lett. 2002, 43: 4993 - 12
Pore DM.Desai UV.Mane RB.Wadgaonkar PP. Synth. Commun. 2004, 34: 2135 - 13
Firouzabadi H.Iranpoor N.Hazarkhani H. Synth. Commun. 2004, 34: 3623 - 14
Habibi MH.Tangestaninejad S.Mohammadpoor-Baltork I.Mirkhani V.Yadollahi B. Tetrahedron Lett. 2001, 42: 2851 - 15
Kumar P.Dinesh CV.Reddy RS.Pandey B. Synthesis 1993, 1069 -
16a
Shirini F.Zolfigol MA.Mollarazi E. Lett. Org. Chem. 2005, 2: 718 -
16b
Zolfigol MA.Azarifar D.Maleki B. Tetrahedron Lett. 2004, 45: 2181 -
16c
Zolfigol MA.Shirini F.Ghorbani CA. Synthesis 2006, 2043 - 17
Zolfigol MA.Ghaemi E.Madrakian E.Ghorbani CA. Mendeleev Commun. 2006, 41 - 18
Azarifar D.Zolfigol MA.Maleki B. Bull. Korean Chem. Soc. 2004, 25: 1 - 19
Alam A.Takaguchi Y.Stuboi S. Synth. Commun. 2005, 35: 1329 - 20
Zolfigol MA.Nasr-Isfahani H.Mallakpour S.Safaiee M. Synthesis 2005, 761 - 21
Zolfigol MA.Khazaei A.Ghorbani CA.Rostami A.Hajjami M. Catal. Commun. 2006, 7: 399