Abstract
Exposure of ketones to NaBO3.4H2O/(CF3CO)2O in the presence of a catalytic amount of poly(iodostyrene) afforded α-hydroxy ketones in good yield, with potential applications in the construction of α-hydroxy ketone subunit in natural product synthesis.
References
1.
Davis F.A.
, and
Chen B.C.
, Chem. Rev. , 1992 , 92 , 919 .
2.
Lee J.C.
,
Jin Y.S.
, and
Choi J.H.
, Chem. Commun. , 2001 , 956 .
3.
Knight R.L.
, and
Leeper F.J.
, J. Chem. Soc. Perkin Trans. , 1 , 1998 , 1891 .
4.
Hashiyama T.
,
Morikawa K.
, and
Sharpless K.B.
, J. Org. Chem. , 1992 , 57 , 5067 .
5.
Koike T.
,
Murata K.
, and
Ikariya T.
, Org. Lett. , 2000 , 2 , 3833 .
6.
Rubottom G.M.
,
Vazquez M.A.
, and
Pelegria D.R.
, Tetrahedron Lett. , 1974 , 15 , 4319 .
7.
Paquette L.A.
,
Lin H.S.
, and
Gallucci J.C.
, Tetrahedron Lett. , 1987 , 28 , 1363 .
8.
Jefford C.W.
, and
Rimbaut C.G.
, J. Am. Chem. Soc. , 1978 , 100 , 6515 .
9.
Friedrich E.
, and
Lutz W.
, Angew. Chem., Int. Ed. Engl. , 1977 , 16 , 413 .
10.
McCormick J.P.
,
Tamasik W.
, and
Johnson M.W.
, Tetrahedron Lett. , 1981 , 22 , 607 .
11.
Rubottom G.M.
,
Gruber J.M.
, and
Mong G.M.
, J. Org. Chem. , 1976 , 41 , 1673 .
12.
Zhou W.S.
,
Jiang B.
, and
Pan X.F.
, J. Chem. Soc., Chem. Commun. , 1988 , 791 .
13.
Ley S.V.
,
Thomas A.W.
, and
Finch H.
, J. Chem. Soc., Perkin Trans. 1 , 1999 , 669 .
14.
Moriarty R.M.
,
Berglund B.A.
, and
Penmasta R.
, Tetrahedron Lett. , 1992 , 33 , 6065 .
15.
Joseph H.B.
, and
Anbazhagan N.
, Synthesis , 1988 , 12 , 980 .
16.
Ochiai M.
,
Takeuchi Y.
,
Katayama T.
,
Sueda T.
, and
Miyamoto K.
, J. Am. Chem. Soc. , 2005 , 127 , 12244 .
17.
Togo H.
,
Nogami G.
, and
Yokoyama M.
, Synlett , 1998 , 534 .
18.
Chen D.J.
, and
Chen Z.C.
, Synth. Commun. , 2001 , 31 , 421 .
19.
Wang G.P.
, and
Chen Z.C.
, Synth. Commun. , 1999 , 29 , 2859 .
20.
Tohma H.
,
Morioka H.
,
Takizawa S.
,
Arisawa M.
, and
Kita Y.
, Tetrahedron , 2001 , 57 , 345 .
21.
Schadt F.
,
Bently T.
, and
Schleyer P.v.R.
, J. Am. Chem. Soc. , 1976 , 98 , 7667 .
22.
Moriarty R.M.
,
Prakash O.
, and
Duncan M.P.
, Synthesis , 1985 , 10 , 943 .
23.
Demir A.S.
,
Ayhan P.
,
Igdir A.C.
, and
Duygu A.N.
, Tetrahedron , 2004 , 60 , 6509 .
24.
Sugiura A.
,
Kepner R.E.
, and
Webb A.D.
, J. Org. Chem. , 1962 , 27 , 773 .