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Synthesis 2008(3): 352-354
DOI: 10.1055/s-2008-1032034
DOI: 10.1055/s-2008-1032034
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Coupling of Aldehydes, Amines, and Trimethyl Phosphite Promoted by Amberlyst-15: Highly Efficient Synthesis of α-Aminophosphonates
Further Information
Received
14 September 2007
Publication Date:
10 January 2008 (online)
Publication History
Publication Date:
10 January 2008 (online)
Abstract
A three-component reaction promoted by Amberlyst-15 of an amine, an aldehyde, and trimethyl phosphite (Kabachnik-Fields reaction) in one pot under mild conditions affords the corresponding α-aminophosphonate in high yield after a short reaction time at ambient temperature.
Key words
amines - phosphonates - Amberlyst-15 catalysis - nucleophilic additions - multicomponent reactions
-
1a
Sikosrki JA.Miller MJ.Braccolino DS.Cleary DG.Corey SD.Ream JE.Schnur D.Shah A.Walker MC. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 76: 375 -
1b
Stowasser B.Budt K.-H.Jian-Qi L.Peyman A.Ruppert D. Tetrahedron Lett. 1992, 33: 6625 -
1c
Atherton FR.Hassall CH.Lambert RW. J. Med. Chem. 1986, 29: 29 -
1d
Peyman A.Budt K.-H.Paning JS.Stowasser B.Ruppert D. Tetrahedron Lett. 1992, 33: 4549 -
1e
Meyer JH.Barlett PA. J. Am. Chem. Soc. 1998, 120: 4600 -
1f
Maier L. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 53: 43 -
1g
Maier L.Spoerri H. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 61: 69 -
1h
Emsley J.Hall D. Chemistry of Phosphorus Harper & Row; London: 1976. p.494 -
2a
Maier L.Lea PJ. Phosphorus Sulfur Relat. Elem. 1983, 17: 1 -
2b
Giannousis PP.Bartlett PA. J. Med. Chem. 1987, 30: 1603 -
2c
Gancarz R.Wieczorek JS. Synthesis 1977, 625 -
2d
Baylis EK.Campbell CD.Dingwall JG. J. Chem. Soc., Perkin Trans. 1 1984, 2845 -
2e
Hilderbrand RL. The Role of Phosphonates in Living Systems CRC Press; Boca Raton USA: 1982. -
2f
Kafarski P.Lejczak B. Phosphorus Sulfur Relat. Elem. 1991, 63: 193 - 3
Pudovik AN. Dokl. Akad. Nauk SSSR 1952, 83: 865 ; Chem. Abstr. 1953, 47, 4300 - 4
Petrov KA.Chauzov VA.Erkhina TS. Usp. Khim. 1974, 43: 2045 ; Chem. Abstr. 1975, 82, 449 -
5a
Laschat S.Kunz H. Synthesis 1992, 90 -
5b
Yadav JS.Reddy BVS.Raj S.Reddy KB.Prasad AR. Synthesis 2001, 2277 -
5c
Zon J. Pol. J. Chem. 1981, 55: 643 -
5d
Ha HJ.Nam GS. Synth. Commun. 1992, 22: 1143 - 6
Yokomatsu T.Yoshida Y.Shibuya S. J. Org. Chem. 1994, 59: 7930 -
7a
Heydari A.Hamadi H.Pourayoubi M. Catal. Commun. 2007, 8: 1224 -
7b
Bhagat S.Chakraborti AK. J. Org. Chem. 2007, 72: 1263 -
7c
Heydari A.Arefi A. Catal. Commun. 2007, 8: 1023 -
7d
Bhattacharya AK.Kaur T. Synlett 2007, 745 -
7e
Manabe K.Kobayashi S. Chem. Commun. 2000, 669 -
7f
Qian C.Huang T. J. Org. Chem. 1998, 63: 4125 -
7g
Ranu BC.Hajra A.Jana J. Org. Lett. 1999, 1: 1141 -
7h
Xu F.Luo Y.Deng M.Shen Q. Eur. J. Org. Chem. 2003, 4728 -
7i
Firouzabadi H.Iranpoor N.Sobhani S. Synthesis 2004, 2692 -
7j
Azizi N.Saidi MR. Eur. J. Org. Chem. 2003, 4430 -
7k
Heydari A.Karimian A.Ipaktschi J. Tetrahedron Lett. 1998, 39: 6729 -
7l
Chandrasekhar S.Prakash SJ.Jagadeshwar V.Narsihmulu C. Tetrahedron Lett. 2001, 42: 5561 -
7m
Kaboudin B.Nazari R. Tetrahedron Lett. 2001, 42: 8211 -
7n
Akiyama T.Sanada M.Fuchibe K. Synlett 2003, 1463 -
7o
Yadav JS.Reddy BVS.Madan C. Synlett 2001, 1131 -
7p
Kudrimoti S.Bommena Roa V. Tetrahedron Lett. 2005, 46: 1209 - 8
Ko S.Yao CF. Tetrahedron Lett. 2006, 47: 8827 -
9a
Tian Q.Zhang S.Yu Q.He MB.Yang JS. Tetrahedron 2007, 63: 2142 -
9b
Sabou R.Hoelderich WF.Ramprasad D.Weinand R. J. Catal. 2005, 232: 34 -
9c
Yadav JS.Subba Reddy BV.Vishnumurthy P. Tetrahedron Lett. 2005, 46: 1311 -
9d
Honkela ML.Root A.Lindblad M.Krause AOI. Appl. Catal., A 2005, 295: 216 - 10
Kaboudin B.Moradi K. Tetrahedron Lett. 2005, 46: 2989 - 11
Zhang W.Zou JP.Mu XJ. Tetrahedron Lett. 2006, 47: 1125