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 2010(12): 2057-2062
DOI: 10.1055/s-0029-1218728
DOI: 10.1055/s-0029-1218728
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Mild and Efficient Catalytic Mannich-Type Reaction as a Simple Access to N-Benzyloxycarbonyl β-Amino Ketones [¹]
Further Information
Received
26 February 2010
Publication Date:
12 April 2010 (online)
Publication History
Publication Date:
12 April 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201012/lookinside/thumbnails/10.1055-s-0029-1218728-1.jpg)
Abstract
N-Benzyloxycarbonylamino sulfones react with aromatic ketones in the presence of catalytic amount of boron trifluoride-diethyl ether at room temperature to afford the corresponding protected β-amino ketones in high yields (71-87%).
Key words
α-amido sulfones - stable imine precursors - aromatic ketones - BF3˙OEt2 - Lewis acids - β-amino ketones
Part 200 in the series ‘Studies on Novel Synthetic Methodologies’.
-
2a
Arend M.Westermann B.Risch N. Angew. Chem. Int. Ed. 1998, 37: 1044 -
2b
Liu M.Sibi MP. Tetrahedron 2002, 58: 7991 -
3a
Casimir JR.Turetta C.Ettouati L.Paris J. Tetrahedron Lett. 1995, 36: 4797 -
3b
Godfrey AC.Brooks DA.Hay LA.Peters M.McCarthy JR.Mitchell D. J. Org. Chem. 2003, 68: 2623 -
4a
Kobayashi S.Ishitani S. Chem. Rev. 1999, 99: 1069 -
4b
Trost BM.Terrell LR. J. Am. Chem. Soc. 2003, 125: 338 -
4c
Joshi NS.Whitaker LR.Francis MB. J. Am. Chem. Soc. 2004, 126: 15942 - 5
Wani MC.Taylor HL.Wall ME.Coggon P.McPhail A.-T. J. Am. Chem. Soc. 1971, 93: 2325 -
6a
List B. J. Am. Chem. Soc. 2000, 122: 9336 -
6b
Xu L.-W.Xia C.-G.Li L. J. Org. Chem. 2004, 69: 8482 -
6c
Cordova A. Acc. Chem. Res. 2004, 37: 102 -
6d
Ollevier T.Nadeau E. J. Org. Chem. 2004, 69: 9292 -
6e
Phukan P.Kataki D.Chakraborthy P. Tetrahedron Lett. 2006, 47: 5523 -
6f
Das B.Majhi A.Chowdhury N.Reddy KR.Ravikanth B. Chem. Lett. 2007, 36: 1106 -
6g
Das B.Majhi A.Reddy KR.Suneel K. J. Mol. Catal. A: Chem. 2007, 274: 83 -
6h
Ollevier T.Nadeau E. Org. Biomol. Chem. 2007, 5: 3126 -
7a
Das B.Damodar K.Sashikanth B.Srinivas Y.Kalavathi I. Synlett 2008, 3133 -
7b
Bas B.Damodar K.Bhunia N. J. Org. Chem. 2009, 74: 5607 - 8
Ollevier T.Nadeau E.Eguillon J.-C. Adv. Synth. Catal. 2006, 348: 2080 -
9a
Pearson WH.Lindback AC.Kampf JW. J. Am. Chem. Soc. 1993, 115: 2622 -
9b
Mecozzi T.Petrini M.
J. Org. Chem. 1999, 64: 8970 - 10
Rao IN.Prabhakaran EN.Das SK.Iqbal J. J. Org. Chem. 2003, 68: 4079 - 11
Green TW.Wuts PGM. Protective Groups in Organic Synthesis 2nd ed.: John Wiley; New York: 1999. p.235-236 -
12a
Petrini M. Chem. Rev. 2005, 105: 3949 -
12b
Petrini M.Torregiani E. Synthesis 2007, 159
References
Part 200 in the series ‘Studies on Novel Synthetic Methodologies’.