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 2012(5): 694-698
DOI: 10.1055/s-0031-1289690
DOI: 10.1055/s-0031-1289690
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Nucleophilic Carbene-Mediated Hydrophosphonylation of Aldimines
Further Information
Received
26 October 2011
Publication Date:
03 February 2012 (online)
Publication History
Publication Date:
03 February 2012 (online)
Abstract
Aldimines undergo efficient hydrophosphonylation reactions with dimethyl phosphite in the presence of nucleophilic heterocyclic carbenes (NHCs) as organocatalysts to give the corresponding (α-aminoalkyl)phosphonates in moderate-to-excellent yields.
Key words
catalysis - carbenes - imines - phosphonylations - phosphonates
- Supporting Information for this article is available online:
- Supporting Information
- For reviews of the biological activity of α-amino phosphonic acids, see:
-
1a
Kafarski P.Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63: 193 -
1b
Hiratake J.Oda J. Biosci., Biotechnol., Biochem. 1997, 61: 211 -
1c
Kafarski P.Lejczak B. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1: 301 -
1d
Grembecka J.Kafarski P. Mini-Rev. Med. Chem. 2001, 1: 133 -
2a
Allen MC.Fuhrer W.Tuck B.Wade R.Wood JM. J. Med. Chem. 1989, 32: 1652 -
2b
Bartlett PA.Hanson JE.Giannousis PG. J. Org. Chem. 1990, 55: 6268 -
2c
Oleksyszyn J.Powers JC. Biochemistry 1991, 30: 485 -
2d
Smith WW.Bartlett PA. J. Am. Chem. Soc. 1998, 120: 4622 - 3
Hirschmann R.Smith AB.Taylor CM.Benkovic PA.Taylor SD.Yager KM.Sprengeler PA.Venkovic SJ. Science (Washington, D. C.) 1994, 265: 234 -
4a
Allen JG.Atherton FR.Hall MJ.Hassall CH.Holmes SW.Lambert RW.Nisbet LJ.Ringrose PS. Nature (London) 1978, 272: 56 -
4b
Atherton FR.Hassall CH.Lambert RW. J. Med. Chem. 1986, 29: 29 -
4c
Pratt RF. Science (Washington, D. C.) 1989, 246: 917 - 5
Lejczak B.Kafarski P.Sztajer H.Mastarlerz P. J. Med. Chem. 1986, 29: 2212 -
6a
Stowasser B.Budt K.-H.Jian-Qi L.Peyman A.Ruppert D. Tetrahedron Lett. 1992, 33: 6625 -
6b
Alonso E.Alonso E.Solís A.del Pozo C. Synlett 2000, 698 - For reviews, see:
-
7a
Pudovik AN.Konovalova IV. Synthesis 1979, 81 -
7b
Kolodiazhnyi OI. Tetrahedron: Asymmetry 1998, 9: 1279 - For recent reviews see:
-
8a
Ma J.-A. Chem. Soc. Rev. 2006, 35: 630 -
8b
Merino P.López EM.Herrera RP. Adv. Synth. Catal. 2008, 350: 1195 - For recent examples of aminophosphonylation reactions see:
-
8c
Gröger H.Saida Y.Arai S.Martens J.Sasai Hiroaki.Shibasaki M. Tetrahedron Lett. 1996, 37: 9291 -
8d
Gröger H.Saida Y.Sasai H.Yamaguchi K.Martens J.Shibasaki M. J. Am. Chem. Soc. 1998, 120: 3089 -
8e
Saito B.Katsuki T. Angew. Chem. Int. Ed. 2005, 44: 4600 -
8f
Saito B.Egami H.Katsuki T. J. Am. Chem. Soc. 2007, 129: 1978 -
8g
Palacios F.Olszewski TK.Vicario J. Org. Biomol. Chem. 2010, 8: 4255 - 9
Joly GD.Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 4102 -
10a
Akiyama T.Morita H.Itoh J.Fuchibe K. Org. Lett. 2005, 7: 2583 -
10b
Akiyama T.Morita H.Bachu P.Mori K.Yamanaka M.Hirata T. Tetrahedron 2009, 65: 4950 -
10c
Shi F.-Q.Song B.-A. Org. Biomol. Chem. 2009, 7: 1292 -
11a
Pettersen D.Marcolini M.Bernardi L.Fini F.Herrera RP.Sgarzani V.Ricci A. J. Org. Chem. 2006, 71: 6269 -
11b
Nakamura S.Nakashima H.Yamamura A.Shibata N.Torua T. Adv. Synth. Catal. 2008, 350: 1209 -
11c
Nakamura S.Hayashi M.Hiramatsu Y.Shibata N.Funahashi Y.Toru T. J. Am. Chem. Soc. 2009, 131: 18240 - For recent reviews, see:
-
12a
Enders D.Balensiefer T. Acc. Chem. Res. 2004, 37: 534 -
12b
Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506 -
12c
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606 -
12d
Marion N.Díez-González S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988 -
12e
Nair V.Vellalath S.Babu BP. Chem. Soc. Rev. 2008, 37: 2691 - 13
Song JJ.Gallou F.Reeves JT.Tan ZL.Yee NK.Senanayake CH. J. Org. Chem. 2006, 71: 1273 -
14a
Zhang J.Du G.-F.Xu Y.-K.He L.Dai B. Tetrahedron Lett. 2012, in press -
14b
Suzuki Y.Abu Bakar MD.Muramatsu K.Sato M. Tetrahedron 2006, 62: 4227 -
14c
Suzuki Y.Muramatsu K.Yamauchi K.Morie Y.Sato M. Tetrahedron 2006, 62: 302 -
14d
Kano T.Sasaki K.Konishi T.Mii H.Maruoka K. Tetrahedron Lett. 2006, 47: 4615 -
14e
Fukuda Y.Maeda Y.Ishii S.Kondo K.Aoyama T. Synthesis 2006, 589 -
14f
Fukuda Y.Kondo K.Aoyama T. Synthesis 2006, 2649 -
14g
Fukuda Y.Maeda Y.Kondo K.Aoyama T. Synthesis 2006, 1937 -
14h
Fukuda Y.Maeda Y.Kondo K.Aoyama T. Chem. Pharm. Bull. 2006, 54: 397 -
15a
Song J.Tan Z.Reeves JT.Yee NK.Senanayake CH. Org. Lett. 2007, 9: 1013 -
15b
Du G.-F.He L.Gu C.-Z.Dai B. Synlett 2010, 2513 -
16a
Wu J.Sun X.Xia HG. Eur. J. Org. Chem. 2005, 4769 -
16b
Wu J.Sun XY.Ye SQ.Sun W. Tetrahedron Lett. 2006, 47: 4813 -
16c
Sun X.Ye S.Wu J. Eur. J. Org. Chem. 2006, 4787 -
16d
Liu YK.Li R.Yue L.Li BJ.Chen YC.Wu Y.Ding LS. Org. Lett. 2006, 8: 1521 - 17
Cai Z.-H.Du G.-F.He L.Gu C.-Z.Dai B. Synthesis 2011, 2073 - 18
Arduengo AJ.Krafczyk R.Schmutzler R.Craig HA.Goerlich JR.Marshall WJ.Unverzagt M. Tetrahedron 1999, 55: 14523 -
19a
Song JJ.Tan ZL.Reeves JT.Fandrick DR.Yee NK.Senanayake CH. Org. Lett. 2008, 10: 877 -
19b
Movassaghi M.Schmidt MA. Org. Lett. 2005, 7: 2453 - 20
He L.Jian T.-Y.Ye S. J. Org. Chem. 2007, 72: 7466 - 21
Das B.Balasubramanyam P.Krishnaiah M.Veeranjaneyulu B.Reddy GC. J. Org. Chem. 2009, 74: 4393