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Synthesis 2004(13): 2191-2195
DOI: 10.1055/s-2004-829197
DOI: 10.1055/s-2004-829197
PAPER
© Georg Thieme Verlag Stuttgart · New York
TMSCl-Promoted Transition Metal-Catalyzed Aza-Michael Reactions of Chalcones with Carbamates
Further Information
Received
23 April 2004
Publication Date:
13 August 2004 (online)
Publication History
Publication Date:
13 August 2004 (online)
Abstract
An improved strategy, which uses transition metals as effective catalyst in the presence of Me3SiCl, has been developed for the conjugate addition of chalcones with unactivated weakly nucleophilic carbamates.
Key words
conjugate addition - aza-Michael reaction - carbamate - enone - transition metal - TMSCl
-
1a
Drury WJ.Ferraris D.Cox C.Young B.Leckta T. J. Am. Chem. Soc. 1998, 120: 11006 -
1b
Hagiwara E.Fujii A.Sodeoka M. J. Am. Chem. Soc. 1998, 120: 2474 -
1c
Abele S.Seebach D. Eur. J. Org. Chem. 2000, 6: 1 -
1d
Varala R.Alam MM.Adapa S. Synlett 2003, 720 -
1e
Fringuelli F.Pizzo F.Rucci M.Vaccaro L. J. Org. Chem. 2003, 68: 7041 -
1f
Duursma A.Minnaard AJ.Feringa BL. J. Am. Chem. Soc 2003, 125: 3700 -
1g
Gnad F.Reiser O. Chem. Rev. 2003, 103: 1603 -
2a
Gaunt MJ.Spencer JB. Org. Lett. 2001, 3: 25 -
2b
Wabnitz TC.Spencer JB. Tetrahedron Lett. 2002, 43: 3891 -
2c
Kobayashi S.Kakumoto K.Sugiura M. Org. Lett. 2002, 4: 1319 -
2d
Jin XL.Sugihara H.Daikai K.Tateishi H.Jin YZ.Furuno H.Inanaga J. Tetrahedron 2002, 58: 8321 -
2e
Xu LW.Xia CG.Li JW.Zhou SL. Synlett 2003, 2246 -
2f
Sibi MP.Prabagaran N.Ghorpade SG.Jasperse CP. J. Am. Chem. Soc. 2003, 125: 11796 -
2g
Xu LW.Li JW.Xia CG.Zhou SL.Hu XX. Synlett 2003, 2425 -
2h
Yamagiwa N.Matsunaga S.Shibasaki M. J. Am. Chem. Soc. 2003, 125: 16178 -
3a
Enders D.Muller SF.Raabe G. Angew. Chem. Int. Ed. 1999, 38: 195 -
3b
Gaunt MJ.Spencer JB. Org. Lett. 2001, 3: 25 -
3c
Enders D.Wallert S. Synlett 2002, 304 -
3d
Sani M.Bruche L.Chiva G.Fustero S.Piera J.Volonterio A.Zanda M. Angew. Chem. Int. Ed. 2003, 42: 2060 -
3e
Volonterio A.Zanda M. Tetrahedron 2003, 44: 8549 -
3f
Xu LW.Li JW.Xia CG. New J. Chem. 2004, 183 -
3g
Xu LW.Li L.Xia CG.Zhou SL.Li JW. Tetrahedron Lett. 2004, 45: 1219 -
4a
Perlmutter P. Conjugate Addition Reactions in Organic Synthesis Pergamon; New York: 1992. p.114 -
4b
Perez M.Pleixates R. Tetrahedron 1995, 51: 8355 -
4c
Asao N.Shimada T.Sudo T.Tsukada N.Yazawa K.Gyoung YS.Yamamoto Y. J. Org. Chem. 1997, 62: 6274 ; and references cited therein -
4d
Bull SD.Davies SG.Delgado-Ballester S.Fenton G.Kelly PM.Smith AD. Synlett 2000, 1257 -
4e
Fadini L.Togni A. Chem. Commun. 2003, 30 -
4f
Sani M.Bruche L.Chiva G.Fustero S.Piera J.Volonterio A.Zanda M. Angew. Chem. Int. Ed. 2003, 42: 2060 - 5
Matsubara S.Yoshioka M.Utimoto K. Chem. Lett. 1994, 827 - 6
Loh TP.Wei LL. Synlett 1998, 975 -
7a
Kawatsura M.Hartwig JF. Organometallics 2001, 20: 1960 -
7b
Sibi MP.Manyem S. Tetrahedron 2000, 56: 8033 -
7c
Zhuang W.Hazell RG.Jørgensen KA. Chem. Commun. 2001, 1240 -
7d
Sibi MP.Liu M. Org. Lett. 2000, 2: 3393 -
7e
Sibi MP.Shay JJ.Liu M.Jasperse CP. J. Am. Chem. Soc. 1998, 120: 6615 - 8
Bartoli G.Bosco M.Marcantoni E.Pertrini M.Sambri L.Torregiani E. J. Org. Chem. 2001, 66: 9052 - 9
Srivastava N.Banik BK. J. Org. Chem. 2003, 68: 2109 -
10a
Wabnitz TC.Yu JQ.Spencer JB. Synlett 2003, 1070 -
10b
Wabnitz TC.Spencer JB. Org. Lett. 2003, 5: 2141 -
10c
Xu LW.Li L.Xia CG.Zhou SL.Li JW.Hu XX. Synlett 2003, 2337 -
10d
Xu LW.Xia CG.Hu XX. Chem. Commun. 2003, 2570 -
10e
Enders D.Wallert S.Runsink J. Synthesis 2003, 1856 -
11a
Christoffers J.Oertling H. Tetrahedron 2000, 56: 1339 -
11b
Christoffers J. Eur. J. Org. Chem. 1998, 1259 -
11c
Christoffers J. Chem. Commun. 1997, 943 -
11d
Kim SS.Nehru K.Kim SS.Kim DW.Jung HC. Synthesis 2002, 2484 - Recent work:
-
12a TMSCl as a scavenger:
Fischer S.Groth U.Jeske M.Schulz T. Synlett 2002, 1922 -
12b Chlorotrimethylsilane as additive:
Ito T.Ishino Y.Mizuno T.Iswkawa A.Kobayashi J. Synlett 2002, 2116 -
12c
Johnson CR.Marren TJ. Tetrahedron Lett. 1987, 28: 27 -
12d
Lee PH.Lee HAK.Sung S.Kim S. Tetrahedron Lett. 2001, 42: 37 -
12e
Bunch L.Krogsgaard-Larsen P.Madsen U. Synthesis 2002, 31 -
12f
Bandini M.Fagioli M.Melloni A.Umani-Ronchi A. Synthesis 2003, 397 -
13a
Nakamura E.Matsuzawa S.Horiguchi Y.Kuwajima I. Tetrahedron Lett. 1986, 27: 4092 -
13b
Horiguchi Y.Matsuzawa S.Nakamura E.Kuwajima I. Tetrahedron Lett. 1986, 27: 4025 -
13c
Matsuzawa S.Horiguchi Y.Nakamura E.Kuwajima I. Tetrahedron 1989, 45: 394