183

Darzens glycidic ester condensation

DE-Epoxy esters (glycidic esters) from base-catalyzed condensation of
D-haloesters with carbonyl compounds.
X
R

O
R1

CO2Et

OEt

R1

R
CO2Et

R2

R2
O

OEt

OEt

O
R
CO2Et

R2
OEt

R1
R2

R1

intramolecular

O
1

R2

SN2

R
CO2Et

Example 14

O
+

Cl

CO2Et

t-BuOK, t-BuOH

CO2Et

10C, 8595%
Example 29

O
H3C

t-BuMe2Si

Br

LDA, THF,
78 C then
PhCHO, 90 C

O
H3C

t-BuMe2Si

H
Ph

66%, 90% de

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.
Newman, M. S.; Magerlein, B. J. Org. React. 1949, 5, 413441. (Review).

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3
4
5
6

7
8
9
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12
13
14
15

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Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, vol. 2, pp 409439. (Review).
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