Abstract
A rapid and efficient regioselective α-chlorination of a new series of β-dicarbonyl compounds using a commercial solution of sodium hypochlorite in the presence of K2CO3 in THF at 0 °C, is reported. With prolonged reaction times, α-chloro β-keto esters, bearing an acyl moiety, undergo a tandem chlorination–deacylation reaction, affording the corresponding α-chlorinated esters.
References
1.
De Kimpe
N.
, and
Verhé
R.
, The chemistry of α-haloketones, α-haloaldehydes, and α-haloimines , John Wiley and Sons , New York , 1990 .
2.
Larock
R.C.
, Comprehensive organic transformations , 2nd edn. Wiley-VCH , New York , 1999 .
3.
Oguchi
M.
,
Wada
K.
,
Honma
H.
,
Tanaka
A.
,
Kaneko
T.
,
Sakakibara
S.
,
Ohsumi
J.
,
Serizawa
N.
,
Fujiwara
T.
,
Horikoshi
H.
, and
Fujita
T.
, J. Med. Chem. , 2000 , 43 , 3052 .
4.
Kodomari
M.
,
Aoyama
T.
, and
Suzuki
Y.
, Tetrahedron Lett. , 2002 , 43 , 1717 .
5.
Rudolph
J.
, Tetrahedron , 2000 , 56 , 3161 .
6.
Kunckell
F.
, Chem. Ber. , 1901 , 34 , 637 .
7.
Lohrisch
H.-J.
,
Kopanski
L.
,
Herrmann
R.
,
Schmidt
H.
, and
Steglich
W.
, Liebigs Ann. Chem. , 1986 , 177 .
8.
Dubois
J.-E.
,
Axiotis
G.
, and
Bertounesque
E.
, Tetrahedron Lett. , 1985 , 26 , 4371 .
9.
Burch
H.A.
, J. Med. Chem. , 1972 , 15 , 429 ; N. De Kimpe, W. De Cock and N. Schamp, Synthesis , 1987, 188.
10.
Gilchrist
T.L.
,
Sanchez Romero
O.A.
, and
Wasson
R.C.
, J. Chem. Soc., Perkin Trans. 1 , 1989 , 353 .
11.
Halland
N.
,
Braunton
A.
,
Bachmann
S.
,
Marigo
M.
, and
Jørgensen
K.A.
, J. Am. Chem. Soc. , 2004 , 126 , 4790 .
12.
Wack
H.
,
Taggi
A.E.
,
Hafez
A.M.
,
Drury
W.J.
III
, and
Lectka
T.
, J. Am. Chem. Soc. , 2001 , 123 , 1531 .
13.
Brochu
M.P.
,
Brown
S.P.
, and
Mac Millan
D.W.C.
, J. Am. Chem. Soc. , 2004 , 126 , 4108 .
14.
Halland
N.
,
Lie
M.A.
,
Kjærsgaard
A.
,
Marigo
M.
,
Schiøtt
B.
, and
Jørgensen
K.A.
, Chem. Eur. J. , 2005 , 11 , 7083 .
15.
Marigo
M.
,
Bachmann
S.
,
Halland
N.
,
Braunton
A.
, and
Jørgensen
K.A.
, Angew. Chem., Int. Ed. , 2004 , 43 , 5507 .
16.
Marigo
M.
,
Kumaragurubaran
N.
, and
Jørgensen
K.A.
, Chem. Eur. J. , 2004 , 10 , 2133 .
17.
Bartoli
G.
,
Bosco
M.
,
Carlone
A.
,
Locatelli
M.
,
Melchiorre
P.
, and
Sambri
L.
, Angew. Chem. Int. Ed. , 2005 , 44 , 6219 .
18.
Mei
Y.
,
Bentley
P.A.
, and
Du
J.
, Tetrahedron Lett. , 2008 , 49 , 3802 .
19.
Yang
D.
,
Yan
Y.-L.
, and
Lui
B.
, J. Org. Chem. , 2002 , 67 , 7429 .
20.
Zhang
Y.
,
Shibatomi
K.
, and
Yamamoto
H.
, J. Am. Chem. Soc. , 2004 , 126 , 15038 .
21.
Cui
H-F.
,
Dong
K-Y.
,
Nie
J.
,
Zheng
Y.
, and
Ma
J-A.
, Tetrahedron Lett. , 2010 , 51 , 2374 .
22.
Meshram
H.M.
,
Reddy
P.N.
,
Sadashiv
K.
, and
Yadav
J.S.
, Tetrahedron Lett. , 2005 , 46 , 623 .
23.
Meshram
H.M.
,
Reddy
P.N.
,
Vishnu
P.
,
Sadashiv
K.
, and
Yadav
J.S.
, Tetrahedron Lett. , 2006 , 47 , 991 .
24.
Mendonça
G.F.
,
Sindra
H.C.
,
De Almeida
L.S.
,
Esteves
P.M.
, and
De Mattos
M.C.S.
, Tetrahedron Lett. , 2009 , 50 , 473 .
25.
Baldovini
N.
,
Bertrand
M.-P.
,
Carrière
A.
,
Nouguier
R.
, and
Plancher
J.-M.
, J. Org. Chem. , 1996 , 61 , 3205 .
26.
Meketa
M.L.
,
Mahajan
Y.R.
, and
Weinreb
S.M.
, Tetrahedron Lett. , 2005 , 46 , 4749 .
27.
Shi
X.-X.
, and
Dai
L.-X.
, J. Org. Chem. , 1993 , 58 , 4596 .
28.
Rezgui
F.
, and
El Gaïed
M.M.
, Tetrahedron , 1997 , 53 , 15711 .
29.
Mhasni
O.
, and
Rezgui
F.
, Tetrahedron Lett. , 2010 , 51 , 586 .
30.
Rezgui
F.
, and
El Gaïed
M.M.
, Tetrahedron Lett. , 1998 , 39 , 5965 .
31.
Rezgui
F.
, and
El Gaïed
M.M.
, J. Chem. Res., (S) , 1999 , 510 .
32.
Jmour
A.
, and
Rezgui
F.
, J. Chem. Res. , 2009 , 642 .
33.
Stotter
P.L.
, and
Hill
K.A.
, Tetrahedron Lett. , 1972 , 13 , 4067 .
34.
Mignani
G.
,
Morel
D.
, and
Grass
F.
, Tetrahedron Lett. , 1987 , 28 , 5505 .
35.
Zhu
J.
,
You
L.
,
Zhao
S.X.
,
White
B.
,
Chen
J.G.
, and
Skonezny
P.M.
, Tetrahedron Lett. , 2002 , 43 , 7585 .
36.
Aoyama
T.
,
Takidoa
T.
, and
Kodomari
M.
, Tetrahedron Lett. , 2004 , 45 , 1873 .