Abstract
The asymmetric synthesis of both (R)-and (S)-arundic acid has been achieved via the key step of a stereoselective alkylation reaction using non-cross-linked polystyrene (NCPS) supported (4R)- and (4S)-2-phenylimino-2-oxazolidine as chiral auxiliaries. This method is efficient (both enantiomers were obtained in 99% ee and 60% overall yield) and the chiral auxiliaries can be recovered quantitatively by simple filtration.
References
1.
Tateishi N.
,
Ohno H.
,
Kishimoto K.
, and
Ohuchida S.
, 1995 , Japan Patent 7-316092.
2.
Matsui T.
,
Mori T.
,
Tateishi N.
,
Kagamiishi Y.
,
Satoh S.
,
Katsube N.
,
Morikawa E.
,
Morimoto T.
,
Ikuta F.
, and
Asano T.
, J. Cereb. Blood Flow Metab. , 2002 , 22 , 711 .
3.
Tateishi N.
,
Mori T.
,
Kagamiishi Y.
,
Satoh S.
,
Katsube N.
,
Morikawa E.
,
Morimoto T.
,
Matsui T.
, and
Asano T.
, J. Cereb. Blood Flow Metab. , 2002 , 22 , 723 .
4.
Kishimoto K.
, and
Nakai H.
1995 , Japan Patent 7-98328.
5.
Hasegawa T.
,
Kawanaka Y.
,
Kasamatsu E.
,
Ohta C.
,
Nakabayashi K.
,
Okamoto M.
,
Hamano M.
,
Takahashi K.
,
Ohuchida S.
, and
Hamada Y.
, Org. Process. Res. Dev. , 2005 , 9 , 774 .
6.
Kishimoto K.
, and
Nakai H.
, 1995 , Japan Patent 7-102693.
7.
Hasegawa T.
, and
Yamamoto H.
, Bull. Chem. Soc. Jpn. , 2000 , 73 , 423 .
8.
Hasegawa T.
,
Kawanaka Y.
,
Kasamatsu E.
,
Iguchi Y.
,
Yonekawa Y.
,
Okamoto M.
,
Ohta C.
,
Hashimoto S.
, and
Ohuchida S.
, Org. Process. Res. Dev. , 2003 , 7 , 168 .
9.
Hasegawa T.
, and
Yamamoto H.
, Synthesis , 2003 , 1181 .
10.
Garcia J.M.
,
Odriozola J.M.
,
Lecumberri A.
,
Razkin J.
, and
Gonzalez A.
, Tetrahedron , 2008 , 64 , 10664 .
11.
Pelotier B.
,
Holmes T.
, and
Piva O.
, Tetrahedron: Asymmetry , 2005 , 16 , 1513 .
12.
Goswami D.
, and
Chattopadhyay A.
, Lett. Org. Chem. , 2006 , 12 , 922 .
13.
Fernandes R.A.
,
Dhall A.
, and
Ingle A.B.
, Tetrahedron Lett. , 2009 , 50 , 5903 .
14.
Fernandes R.A.
,
Ingle A.B.
, and
Chaudhari D.A.
, Eur. J. Org. Chem. , 2012 , 1047 .
15.
Afewerki S.
,
Ibrahem I.
,
Rydfjord J.
,
Breistein P.
, and
Córdova A.
, Chem. Eur. J. , 2012 , 18 , 2972 .
16.
Gualandi A.
,
Emer E.
,
Capdevila M.G.
, and
Cozzi P.G.
Angew. Chem. Int. Ed. , 2011 , 50 , 7842 .
17.
Hu F.Q.
,
Xia D.X.
,
Lu C.F.
,
Chen Z.X.
, and
Yang G.C.
Eur. J. Org. Chem. , 2010 , 5552 .
18.
Lu C.F.
,
Hu F.Q.
,
Chen Z.X.
, and
Yang G.C.
J. Chem. Res. , 2012 , 276 .
