183
Darzens glycidic ester condensation
DE-Epoxy esters (glycidic esters) from base-catalyzed
condensation of D-haloesters with carbonyl compounds.
R CO2Et
X
R1 R2O OEt
OR1
R2 CO2EtR
R
XH
OEt
R
XR1 R2
O
OEt
OOEt
O
R2R
OR1
XCO2Et
OR1
R2 CO2EtR
intramolecular
SN2
Example 14
OCl CO2Et
OCO2Et+
t-BuOK, t-BuOH
10C, 8595%
Example 29
H3C Br
t-BuMe2Si
O LDA, THF, 78 C then H3C
t-BuMe2Si
O OPh
H
H
66%, 90% dePhCHO, 90 C
References
1 Darzens, G. A. Compt. Rend. Acad. Sci. 1904, 139, 1214. George
Auguste Darzens (18671954) born in Moscow, Russia, studied at cole
Polytechnique in Paris and stayed there as a professor.
2 Newman, M. S.; Magerlein, B. J. Org. React. 1949, 5, 413441.
(Review).
184
3 Ballester, M. Chem. Rev. 1955, 55, 283300. (Review). 4 Hunt,
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3791. 6 Rosen, T. Darzens Glycidic Ester Condensation In
Comprehensive Organic Synthesis;
Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, vol. 2,
pp 409439. (Re-view).
7 Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm.
Bull. 1995, 43, 1821. 8 Ohkata, K.; Kimura, J.; Shinohara, Y.;
Takagi, R.; Hiraga, Y. Chem. Commun. 1996,
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Kimura, J.; Shinohara, Y.; Ohba, Y.; Takezono, K.; Hiraga, Y.;
Kojima,
S.; Ohkata, K. J. Chem. Soc., Perkin Trans. 1 1998, 689. 11
Hirashita, T.; Kinoshita, K.; Yamamura, H.; Kawai, M.; Araki, S. J.
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Name Reactions in Heterocyclic
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