Abstract
In the presence of a catalytic amount of KI in combination with H2O2, a convenient catalytic procedure has been developed for the direct preparation of acetoxylactones from alkenoic acids in acetic acid at room temperature which provides the corresponding cyclic products in good yields. This novel methodology mediated by an in situ generated hypervalent iodine intermediate extends the catalytic application of KI in organic synthesis.
Keywords
References
1.
Stang P. J.
, and
Zhdankin V. V.
, Chem. Rev. , 1996 , 96 , 1123 .
2.
Zhdankin V. V.
, and
Stang P. J.
, Chem. Rev. , 2002 , 102 , 2523 .
3.
Okuyama T.
, Acc. Chem. Res. , 2002 , 35 , 12 .
4.
Grushin V. V.
, Chem. Soc. Rev. , 2000 , 29 , 315 .
5.
Ochiai M.
,
Takeuchi Y.
,
Katayama T.
,
Sueda T.
, and
Miyamoto K.
, J. Am. Chem. Soc. , 2005 , 127 , 12244 .
6.
Dohi T.
,
Maruyama A.
,
Yoshimura M.
,
Morimoto K.
,
Tohma H.
, and
Kita Y.
, Angew. Chem. Int. Ed. , 2005 , 44 , 6193 .
7.
Richardson R. D.
, and
Wirth T.
, Angew. Chem. Int. Ed. , 2006 , 45 , 4402 .
8.
Tanaka A.
,
Moriyama K.
, and
Togo H.
, Synlett , 2011 , 1853 .
9.
Uyanik M.
,
Suzuki D.
, and
Yasui T.
, Angew. Chem. Int. Ed. , 2011 , 50 , 5331 .
10.
Krishna Mohan K. V. V.
,
Narender N.
, and
Kulkarni S. J.
, Tetrahedron Lett. , 2004 , 45 , 8015 .
11.
Uyanik M.
,
Okamoto H.
, and
Yasui T.
, Science , 2010 , 328 , 1376 .
12.
Zhou Z. S.
, and
He X. H.
, J. Chem. Res. , 2014 , 38 , 630 .
13.
Ohta H.
,
Sakata Y.
, and
Takeuchi T.
, Chem. Lett. , 1990 , 19 , 733 .
14.
Asensio G.
,
Andreu C.
,
Boix-Bernardini C.
,
Mello R.
, and
Gonzalez-Nunez M. E.
, Org. Lett. , 1999 , 1 , 2125 .
15.
Nicoletti D.
,
Ghini A. A.
, and
Burton G.
, J. Org. Chem. , 1996 , 61 , 6673 .
16.
Tiecco M.
,
Testaferri L.
,
Tingoli M.
, and
Bartoli D.
, Tetrahedron , 1990 , 46 , 7139 .
17.
Ha H.-J.
,
Yoon K.-N.
,
Lee S.-Y.
,
Park Y.-S.
,
Lim M.-S.
, and
Yim Y.-G.
, J. Org. Chem. , 1998 , 63 , 8062 .
18.
Tiecco M.
,
Testaferri L.
, and
Tingoli M.
, Tetrahedron , 1993 , 49 , 5351 .
19.
Wang S.
,
Chen G.
,
Kayser M. M.
,
Iwaki H.
,
Lau P. C. K.
, and
Hasegawa Y.
, Can. J. Chem. , 2002 , 80 , 613 .
20.
Kamal A.
,
Khan M. N. A.
,
Reddy K. S.
,
Srikanth Y. V. V.
, and
Krishnaji T.
, Tetrahedron Lett. , 2007 , 48 , 3813 .