Abstract
N-heterocyclic carbenes have been successfully used as ligands in organometallic catalysis, and also as organocatalysts in different reactions. A series of novel chiral unsymmetrical imidazolinium salts which are precursors of N-heterocylic carbenes were synthesised effectively from the relatively inexpensive amino acid L-phenylalanine in six steps. These chiral unsymmetrical imidazolinium bromides were fully characterised by NMR and elemental analysis, and their specific rotations were obtained.
References
1.
Arduengo A.J.
,
Harlow R.L.
,
Kline M.K.
, J. Am. Chem. Soc. , 1991 , 113 , 361 .
2.
Herrmann W.A.
, Angew. Chem. Int. Ed. , 2002 , 41 , 1290 .
3.
Díez-González S.
,
Marion N.
,
Nolan S.P.
, Chem. Rev. , 2009 , 109 , 3612 .
4.
Nolan S.P.
, Acc. Chem. Res. , 2011 , 44 , 91 .
5.
Würtz S.
, and
Glorius F.
, Acc. Chem. Res. , 2008 , 41 , 1523 .
6.
Weskamp T.
,
Schattenmann W.C.
,
Spiegler M.
,
Herrmann W.A.
, Angew. Chem. Int. Ed. , 1998 , 37 , 2490 .
7.
Hoveyda A.H.
,
Schrock R.R.
, Chem. Eur. J. , 2001 , 7 , 945 .
8.
Trnka T.M.
,
Grubbs R.H.
, Acc. Chem. Res. , 2001 , 34 , 18 .
9.
Hillier A.C.
,
Grasa G.A.
,
Viciu M.S.
,
Lee H.M.
,
Yang C.
, and
Nolan S.P.
, J. Organomet. Chem. , 2002 , 653 , 69 .
10.
Lee H.M.
,
Jiang T.
,
Stevens E.D.
,
Nolan S.P.
, Organometallics , 2001 , 20 , 1255 .
11.
Marion N.
,
Díez-González S.
,
Nolan S.P.
, Angew. Chem. Int. Ed. , 2007 , 46 , 2988 .
12.
Enders D.
,
Balensiefer T.
, Acc. Chem. Res. , 2004 , 37 , 534 .
13.
Enders D.
,
Niemeier O.
,
Henseler A.
, Chem. Rev. , 2007 , 107 , 5606 .
14.
Gade L.H.
,
Bellemin-Laponnaz S.
, Coord. Chem. Rev. , 2007 , 251 , 718 .
15.
Mata J.A.
,
Poyatos M.
,
Peris E.
, Coord. Chem. Rev. , 2007 , 251 , 841 .
16.
Winn C.L.
,
Guillen F.
,
Pytkowicz J.
,
Roland S.
,
Mangeney P.
,
Alexakis A.
, J. Organomet. Chem. , 2005 , 690 , 5672 .
17.
Merzouk M.
,
Moore T.
,
Williams N.A.
, Tetrahedron Lett. , 2007 , 48 , 8914 .
18.
Williams N.A.
,
Merzouk M.
,
Hitchcock P.B.
, Inter. J. Inorg. Chem. , 2010 , http://downloads.hindawi.com/journals/ijic/2010/628639.pdf, doi: 10.1155/2010/628639.
19.
Ogata K.
,
Atsuumi Y.
,
Shimada D.
,
Fukuzawa S.
, Angew. Chem. Int. Ed. , 2011 , 50 , 5896 .
20.
Rix D.
,
Labat S.
,
Toupet L.
,
Crevisy C.
,
Mauduit M.
, Eur. J. Inorg. Chem. , 2009 , 13 , 1989 .
