Abstract
A novel and efficient method has been developed for the chiral resolution and separation from cis-cyclohexane-1,2-diamine of (±)-cyclohexane-1,2-diamine, which reacts with xylaric acid, a substitute for tartaric acid. This method provides (1R,2R)-cyclohexane-1,2-diamine, and (1S,2S)-cyclohexane-1,2-diamine and cis-cyclohexane-1,2-diamine in good yield with high optical purity.
References
1.
Iihan S.
, J. Chem. Res. , 2009 , 33 , 766 .
2.
Alfonso I.
, Org. Synth. , 2013 , 5 , 51 .
3.
Gao C.Z.
,
Xu G.
, and
Gou S.H.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 6386 .
4.
Gao C.Z.
,
Gou S.H.
,
Fang L.
, and
Zhao J.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 1763 .
5.
Gao C.Z.
,
Gou S.H.
, and
Xu G.
, Chem. Pharm. Bull. , 2011 , 59 , 851 .
6.
Keiji M.
,
Takashi O.
, and
Taichi K.
, Chem. Commun. , 2007 , 15 , 1487 .
7.
Giorgio D.F.
,
Gennadiy I.
, and
Michael W.
, Chem. Soc. Rev. , 2011 , 40 , 1722 .
8.
Chen D.Y.-K.
,
Pouwer R.H.
, and
Richard J.-A.
, Chem. Soc. Rev. , 2012 , 41 , 4631 .
9.
Tokunaga M.
,
Larrow J.F.
,
Kakiuchi F.
, and
Jacobsen E.N.
, Science , 1997 , 277 , 936 .
10.
Smith A.I.
, and
Raleigh N.C.
, PCT Int. Appl. , US3167587.
11.
Larrow J.F.
, and
Jacobsen E.N.
, J. Org. Chem. , 1994 , 59 , 1939 .
12.
Larrow J.F.
, and
Jacobsen E.N.
, Org. Synth. , 2004 , 10 , 96 .
13.
Larrow J.F.
, and
Quigley P.F.
Comprehensive Chirality , 2012 , 9 , 129 .
14.
Peng Z.Y.
,
Zhang K.
, and
Ge J.L.
, PCT Int. Appl. , CN102329241A.
15.
He L.
Shang Dong Hua Gong , 2010 , 39 , 5 .
16.
Galland A.
,
Dupray V.
,
Lafontaine A.
,
Berton B.
,
Sanselme M.
,
Atmani H.
, and
Coquerel G.
Tetrahedron: Asymmetry , 2010 , 21 , 2212 .
17.
Schanz H.J.
,
Linseis M.A.
, and
Gilheany D.G.
, Tetrahedron: Asymmetry , 2003 , 14 , 2763 .
18.
Dag E.
,
Svein M.
,
Yngve S.
, Carbohydrate. Res. , 2007 , 342 , 1992 .
19.
Pushpakiran G.
,
Akihide Y.
,
Kenji M.
,
Devendar R.
,
Kazuya A.
,
Jenkinson S.F.
,
Fleet G.W.J.
,
Ken I.
, Tetrahedron. Lett. , 2010 , 51 , 895 .
20.
Liaw H.M.
,
Kowzic R.L.
,
Eddington J.M.
,
Yang Y.Q.
, PCT Int. Appl. , US6387654.
21.
Paolo D.
,
Paola P.
, and
Stefano R.
, J. Org. Chem. , 2001 , 66 , 4930 .
