Abstract
A variety of epoxides were converted into β-chloroacetates and benzoates by using TMSCl and the corresponding acid anhydride in the presence of a catalytic amount of Cu(OTf)2.
References
1.
For some general reviews on epoxides, see: (a)
Smith J.G.
, Synthesis , 1984 , 629
2.
Rao A.S.
,
Paknikar S.K.
,
Kirtane J.G.
, Tetrahedron , 1983 , 39 , 2323
3.
Rickborn B.
,: Acid Catalysed rearrangments of epoxides. In Comprehensive Organic synthesis ,
Trost B.M.
,
Fleming I.
, (eds.), Pergamon Press , Oxford , 1991 , Vol. 3 , pp. 733 –775 .
4.
(a)
Iranpoor N.
, and
Zeynizadeh B.
, J. Chem. Res. , 1998 , 582
5.
Taniguchi Y.
,
Tanaka S.
,
Kitamura T.
, and
Fujiwara Y.
, Tetrahedron Lett. , 1998 , 39 , 4559
6.
Luzzio F.A.
, and
Bobb R.A.
, Tetrahedron , 1999 , 55 , 1851 .
7.
For other application of Cu(OTf)2 in organic synthesis, see: (a)
Saravanan P.
,
Anand R.V.
, and
Singh V.K.
, Tetrahedron Lett. , 1998 , 39 . 3823
8.
Anand R.V.
,
Saravanan P.
, and
Singh V.K.
, Synlett , 1999 , 415
9.
Saravanan P.
, and
Singh V.K.
, Tetrahedron Lett. , 1999 , 40 . 2611
10.
Sekar G.
, and
Singh V.K.
, J. Org. Chem. , 1999 , 64 , 287
11.
Sekar G.
, and
Singh V.K.
, J. Org. Chem. 1999 , 64 , 2537 .
12.
Murata S.
,
Suzuki M.
, and
Noyori R.
, J. Am. Chem. Soc. , 1979 , 101 , 2738 .
13.
Chandra Kusum L.
,
Saravanan P.
, and
Singh V.K.
, Tetrahedron Lett. , 2001 , 42 , 5309 .
14.
(a)
Hodgson D.M.
,
Witherington J.
, and
Moloney B.A.
, J. Chem. Soc. Perkin Trans. , 1994 , I 3373
15.
Hodgson D.M.
,
Witherington J.
, and
Moloney B.A.
, J. Chem. Soc. Perkin Trans. , 1993 , I 1543 .
16.
Kim H.R.
,
Oh H.S.
,
Park H.J.
,
Kim J.N.
,
Jeon D.J.
, and
Ryu E.K.
, Synth. Commun. , 1998 , 28 , 159 .
17.
Nikitchenko V.S.
,
Sergucher Y.A.
, and
Gutsulyak R.B.
, Russ. J. Gen. Chem. , 1997 , 67 , 489 .