2066
+
DBU,
Scheme 2
a)
were determined by chiral HPLC on Chiralcel OD Daicel column 25 x 0.46 cm,
In summary, we have established the optimal conditions for the kinetic dynamic resolutions of racemic
esters to produce both
enantiomers of glycidates with very high enantioselectivity (up to
This technic
97% ee) using chiral Ru complexes prepared in-situ from
offers news opportunities for the preparation of biologically active products and these studies are currently
under investigation.
Acknowledgements : We thank
(Brazil) for a grant to M. C.
de Andrade. We also thank Dr M.
Y.
Petit and 0.
thank Dr. E.
for helpful discussions. We are also very grateful to Y.
and Dr. R.
for technical assistance (HPLC analysis). We
=
(Hoffman La
and
glycidate.
for samples of
We thank Dr.
Rossey
for providing us analytical
data of the
References and notes
a) Rossey.
L.; Wick, A. E. E.P. 049712; b) Rossey,
Kanerva, L.T.; Sundholm, 0. J. Chem.
K.; Oh-lshi, T. Pharm. Bull. 1993.41.
A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 643-648.
a) Nagao, T.; M.; Nakajima, H. Chem. Pharm. Bull. 1973,
a) Guenard, D.; Gueritte-Vogelein, F.; Potier, P.
G.N.; Drugs. 519; c)
M.; Guenard, D. Gueritte-Voegelin, F. Potier, P.
Zard, L.; Wick, A. E. chiral 92 Proc eedings
Manchester U.K. 1992.51;
Inoue, H.;
Trans
d)
e) Marsuki, K.;
2.
3.
Res. 1993.26, 160-167; b) Sclichenmyer, W.J.;
S. Chem. Eng. News.
Put. Appli. E.P.
d) For
4.
a)
L.; Jacobsen, E. N. J. Org. Chem.
43204323; b) Dcnis, J.-N.;
A.; Greene,
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Chem. 1991.56, 6939-6942;
J.-N.;
A.: Greene, A.E. J. Org. Chem. 1990.57, 1957-1959; d)
J.-N.; Greene, A.E.;
approach to
A.A.;
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e) Review total and semi synthetic
Tetrahedron symposia-in-print,
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Synthesis of
R.A.;
C.; Kim, H.-B.; Liang, F.;
R.J.; Boatman, P.D.;
M.;
Smith,
Kim, S.;
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a) Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. J.
H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K.K.; Gentile, L.N.;
1994,116, and
5.
6.
Trans 1993, 13, 1375-1376; b)
Asymmetry. 43-46; b)
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de Andrade, M.C.: Laffitte, J.A.
J.-P.; Pinel. C.: Ratovelomanana-Vidal. V.;
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S.; S., Patent 8911159 (August 1989); b)
S.; Thorimbert, S.; Laffitte, J.A. Tetrahedron 1991.2, 555-567; c)
Ratovelomanana-Vidal, V.; Pinel, C.; J.A.
this area see: Noyori, R.;
T.; Takemoti. T.: Kumobayashi, H. J. Am. Chem.
M.; Noyori, R. J. Am. Chem. 1993,115,
a) For microbial asymmetric reduction of
0.;
J.-P.; Pinel,
Ratovelomanana-Vidal, V.:
S;
X.;
: Asymmetry.
1994.5, 665-674:
Andrade, MC.;
S.; Pfister, X.; Bischoff, L.; Cairo de
7.
a)
J.-P.:
J.-P.; Pinel, C.;
J.-P.;
S.;
X.;
d) For leading references in
T.; Okhuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa,
N.;
1989,111, 9134-9135 and Kitamura, M.; Tokunaga,
8.
esters see
M.; Buisson, D.;
H.; Ikari, Y.; Oishi, T. Synthesis.
H.; Matsukura, H.; Oishi, T.; Tetrahedron
R.
H.;
R.;
9.
General procedure of hydrogenation:
esters (1 mmol) dissolved in 2 ml of anhydrous solvent were.
into a ml Schlenck tube filled with argon
by
a
times cycle of vacuum/argon at R.T.. This solution was
atmosphere containing
(1
and the chiral diphosphine (1.3
3 times with hydrogen and
The reaction mixture
was immediately placed into an autoclave which was
available from
10
(Received in France 8 December 1994; accepted 25 January 1995)