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Synlett 2002(6): 0883-0886
DOI: 10.1055/s-2002-31919
DOI: 10.1055/s-2002-31919
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Mild Deprotection of Trichloroethyl Carbamates Using Indium Metal
Further Information
Received
20 March 2002
Publication Date:
07 February 2007 (online)
Publication History
Publication Date:
07 February 2007 (online)
Abstract
The trichloroethoxycarbonyl moiety was efficiently removed from carbamates to furnish the corresponding amines using indium metal in good to excellent yields.
Key words
indium - deprotection - amines - 2,2,2-trichloroethyl carbamates - chemoselectivity
- 1
Woodward RB.Heusler K.Gosteli J.Naegeli P.Oppolzer W.Ramage R.Ranganathan S.Vorbrüggen H. J. Am. Chem. Soc. 1966, 88: 852 - 2
Windholz TB.Johnston DBR. Tetrahedron Lett. 1967, 27: 2555 - 3
Dvorak CA.Schmitz WD.Poon DJ.Pryde DC.Lawson JP.Amos RA.Meyers AI. Angew. Chem. Int. Ed. 2000, 39: 1664 - 4
Xie C.Runnegar MTC.Snider BB. J. Am. Chem. Soc. 2000, 122: 5017 - 5
Takayama H.Ichikawa T.Kuwajima T.Kitajima M.Seki H.Aimi N.Nonato MG. J. Am. Chem. Soc. 2000, 122: 8635 - 6
Peschko C.Steglich W. Tetrahedron Lett. 2000, 41: 9477 - 7
Just G.Grozinger K. Synthesis 1976, 457 - 8
Hijfte LV.Little RD. J. Org. Chem. 1985, 50: 3940 - 9
Semmelhack MF.Heinsohn GE. J. Am. Chem. Soc. 1972, 94: 5139 - 10
Overman LE.Freerks RL. J. Org. Chem. 1981, 46: 2833 - 11
Hancock G.Galpin IJ.Morgan BA. Tetrahedron Lett. 1982, 23: 249 - 12
Dong Q.Anderson CE.Ciufolini MA. Tetrahedron Lett. 1995, 36: 5681 - 13
Eckert H.Ugi I. Angew. Chem. Int. Ed. Engl. 1976, 15: 681 - 14
Lakshmikantham MV.Jackson YA.Jones RJ.O’Malley GJ.Ravichandran K.Cava MP. Tetrahedron Lett. 1986, 27: 4687 - 15
Pitts MR.Harrison JR.Moody CJ. J. Chem. Soc., Perkin Trans. 1 2001, 955 ; and references cited therein - 16
Valluri M.Mineno T.Hindupur RM.Avery MA. Tetrahedron Lett. 2001, 42: 7153 - 17
Windholz TB.Johnston DBR. Tetrahedron Lett. 1967, 2555
References
Aldrich Chemical Company. Indium powder, 99.99%. Catalog # 27,795-9.