Abstract
L-cysteine supported on an iron oxide magnetic nanoparticle was prepared by a facile and simple method. The catalyst was effectively applied to the one-pot synthesis of β-amino esters in moderate to good yield. Moreover, the magnetic organocatalyst could be readily recovered and reused up to five times without significant loss of its catalytic activity.
References
1.
Cardillo G.
, and
Tomasini C.
, Chem. Soc. Rev. , 1996 , 25 , 117 .
2.
Rosenblum S.B.
,
Huynj T.
, and
Burnett D.A.
, J. Med. Chem. , 1998 , 41 , 973 .
3.
Muller R.
,
Goesmann H.
, and
Waldmann H.
, Angew. Chem. Int. Ed. , 1999 , 38 , 184 .
4.
Hatano M.
,
Horibe T.
, and
Ishihara K.
, Org. Lett. , 2010 , 12 , 3502 .
5.
Josephsohn N.S.
,
Carswell E.L.
,
Snapper M.L.
, and
Hoveyda A.H.
, Org. Lett. , 2005 , 7 , 2711 .
6.
Zhang H.
,
Mitsumori S.
,
Utsumi N.
,
Imia N.
,
Garcia-Delgado N.
,
Mifud M.
,
Albertshofer K.
,
Cheong P.H.-Y.
,
Houk K.N.
,
Tanaka F.
, and
Barbas C.F.
, J. Am. Chem. Soc. , 2008 , 130 , 875 .
7.
Kobayashi S.
,
Matsubara R.
, and
Kitagawa H.
, Org. Lett. , 2002 , 4 , 143 .
8.
Periasamy M.
,
Suresh S.
, and
Ganesan S.S.
, Tetrahedron Lett. , 2005 , 46 , 5521 .
9.
Komoto I.
, and
Kobayashi S.
, J. Org. Chem. , 2004 , 69 , 680 .
10.
Pandey G.
,
Singh R.P.
,
Garg A.
, and
Singh V.K.
, Tetrahedron Lett. , 2005 , 46 , 2137 .
11.
Lu A.H.
,
Salabas E.L.
, and
Schuth F.
Angew. Chem. Int. Ed. , 2007 , 46 , 1222 .
12.
Perez J.M.
Nat. Nanotechnol. , 2007 , 2 , 535 .
13.
Polshettiwar V.
,
Baruwati B.
, and
Varma R.S.
Chem. Commun. , 2009 , 14 , 1837 .
14.
Polshettiwar V.
, and
Varma R.S.
Tetrahedron , 2010 , 66 , 1091 .
15.
Nasir Baig R.B.
,
Varma R.S.
Green Chem. , 2013 , 15 , 398 .
16.
Gleeson O.
,
Tekoriute R.
,
Gun'ko Y.K.
, and
Connon S.J.
Chem. Eur. J. , 2009 , 15 , 5669 .
17.
Dalaigh C.O.
,
Corr S.A.
,
Gun'ko Y.K.
, and
Connon S.J.
, Angew. Chem. Int. Ed. , 2007 , 46 , 4329 .
18.
Gleeson O.
,
Davies G.L.
,
Peschiulli A.
,
Tekoriute R.
,
Gun'ko Y.K.
, and
Connon S.J.
, Org. Biomol. Chem. , 2011 , 9 , 7929 .
19.
Gawande M.B.
,
Velhinho A.
,
Nogueira I.D.
,
Ghumman C.A.A.
,
Teodoro O.M.N.D.
, and
Branco P.S.
, RSC Adv. , 2012 , 2 , 6144 .
20.
Huang Y.B.
,
Yi W.B.
, and
Cai C.
, J. Fluorine Chem. , 2010 , 131 , 879 .
21.
Wang L.
,
Yi W.B.
, and
Cai C.
, Chem. Commun. , 2011 , 47 , 806 .
22.
Yang Y.
,
Shou W.
, and
Wang Y.
, Tetrahedron , 2006 , 62 , 10079 .
23.
Neelakantan L.
, and
Hartung W.H.
, J. Org. Chem. , 1959 , 24 , 1943 .
24.
Khan A.T.
,
Parvin T.
, and
Choudhury L.H.
, Eur. J. Org. Chem. , 2008 , 834 .