Abstract
The isomers of α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetic acid esters derived from 3-azabicyclo[3,3,1]nonan-9α-ol ((R)-1 and (S)-1) were obtained in high enantiomeric excess by effective stereoselective synthesis from the chiral starting material, (S) or (R)-mandelic acid using pivaldehyde as a sterically hindered reagent
References
1.
(a)
Caner H.
,
Groner E.
,
Lery L.
, and
Agranat I.
Drug Discovery Today , 2004 , 9 , 105 .
2.
Rouhi A.M.
, Chem. Eng. News , 2003 , 81 , 45 .
3.
Richards A.
, and
McCague R.
, Chem. Ind. , 1997 , 422 .
4.
(a)
Mitsuya M.
,
Ogino Y.
,
Ohtake N.
, and
Mase T.
, Tetrahedron , 2000 , 56 , 9901 .
5.
Mitsuya M.
,
Kawakami K.
,
Ogino Y.
,
Miura K.
, and
Mase T.
, Bioorg. Med. Chem. Lett. , 1999 , 9 , 2037 .
6.
(a)
Liu H.
,
Liu C. H.
,
Han X. Y.
,
Zhong B. H.
, and
Liu K. L.
, J. Chem. Res. , 2004 , 482 .
7.
Liu H.
,
Han X. Y.
,
Liu C. H.
,
Zhong B. H.
, and
Liu K. L.
, Anal. Sci. , 2004 , 20 , x121 .
8.
Wu P.J.
, and
Yun L. H.
, Chin. J. Med. Chem. , 1999 , 9 , 102 .
9.
Wang L.
,
Yun L. H.
, and
Zhang Q. K.
, Acta. Pharmaceutica. Sin. , 1996 , 31 , 790 .
10.
Caldwell J.
, Modern Drug Discov. , 1999 , 2 , 51 .
11.
(a)
Ortholand J.Y.
,
Vicart N.
, and
Greiner A.
, J. Org. Chem. , 1995 , 60 , 1880 .
12.
Ott J.
,
Ramos T. G. M.
,
Schmid B.
,
Venanzi L. M.
,
Wang G.
, and
Ward T. R.
, Tetrahedron Lett. , 1989 , 30 , 6151 .
13.
(a)
Lowe A.
,
Drozda J. S. E.
,
McLean S.
,
Bryce D. K.
,
Crawford R. T.
,
Snider R. M.
,
Longo K. P.
,
Nagahisa A.
, and
Tsuchiya M.
, J. Med. Chem. , 1994 , 37 , 2831 .
14.
Ohki R.D.
,
Oida S.
,
Ohashi Y.
,
Yoshida A.
,
Kamoshita K.
, and
Takagi H.
, Chem, Pharm. Bull. , 1974 , 22 , 1014 .
15.
Grover P.T.
,
Bhongle N. N.
,
Wald S. A.
, and
Senanayake C. H.
, J. Org. Chem. , 2000 , 65 , 6283 .
