Abstract
A rapid, safe, and efficient method for the preparation of new carbamate type molecular tweezers based on deoxycholic acid was reported. Eleven new molecular tweezers have been synthesised in good yield(91–96%). The structures of these receptors were confirmed by 1H NMR, IR, MS spectra and elemental analysis. These molecular tweezers not only recognised neutral molecules, but also showed good enantioselectivity for D-amino acid methyl esters.
References
1.
Rebek J.
Jr.
, Science , 1987 , 235 , 1478 .
2.
Zhang X.X.
,
Bradshaw J.S.
, and
Izatt R.M.
, Chem. Rev. , 1997 , 97 , 3313 .
3.
Schmidtchen F.P.
, and
Berger M.
, Chem. Rev. , 1997 , 97 . 1609 .
4.
Guo X.
,
Liu F.
, and
Lu G.Y.
, Chin. J. Org. Chem. , 2005 , 25 , 1021 (in Chinese).
5.
Xu Z.C.
,
Kim S.K.
, and
Yoon Y.
, Chem. Soc. Rev. , 2010 , 39 , 1457 .
6.
Kim K.S.
, and
Kim H.S.
, Tetrahedron , 2005 , 61 , 12366 .
7.
Siracusa L.
,
Hurley F.M.
, and
Dresen S.
, Org. Lett. , 2002 , 4 , 4639 .
8.
Zhao Z.G.
,
Zhang P.Y.
,
Yang Z.X.
, and
Chen S.H.
, Chin. J. Org. Chem. 2005 , 25 , 679 (in Chinese).
9.
Chahar M.
, and
Pandey P.S.
, Tetrahedron , 2008 , 64 , 6488 .
10.
Appukkuttan P.
,
Mehta V.P.
, and
Van der Eycken E.V.
, Chem. Soc. Rev. , 2010 , 39 , 1467 .
11.
Polshettiwar V.
, and
Varma R.S.
, Acc. Chem. Res. , 2008 , 41 , 629 .
12.
Kappe C.O.
, Angew. Chem. Int. Ed. , 2004 , 43 , 6250 .
13.
Dallinger D.
, and
Kappe C.O.
, Chem. Rev. , 2007 , 107 , 2563 .
14.
Wu X.M.
,
Zhao Z.G.
,
Liu X.L.
,
Chen Y.
, and
Zhao X.X.
, Chin. J. Org. Chem. , 2009 , 29 , 956 (in Chinese).
15.
Xiu X.L.
,
Zhao Z.G.
, and
Chen S.H.
, Chin. J. Org. Chem. , 2007 , 27 , 772 (in Chinese).
16.
Zhao Z.G.
,
Liu X.L.
, and
Zhou C.E.
, Chin. Chem. Lett. , 2007 , 18 , 1067 .
17.
Zeng B.T.
,
Zhao Z.G.
,
Zhao X.X.
,
Ye Y.
,
Chen Y.
,
Shi Z.C.
, and
Wu X.M.
, Chin. J. Org. Chem. , 2009 , 29 , 1621 (in Chinese).
18.
Zeng B.T.
,
Zhao Z.G.
,
Liu X.L.
, and
Shi Y.
, Chin. Chem. Lett. , 2008 , 19 , 33 .
19.
Xue C.H.
,
Hu R.
,
Mu Q.M.
,
Li F.
, and
Chen S.H.
, Acta Chim. Sinica. , 2000 , 58 , 717 .
20.
Liu X.L.
,
Zhao Z.G.
, and
Zeng B.T.
, Chin. J. Org. Chem. , 2007 , 27 , 994 (in Chinese).