Abstract
Radical ytterbium trifluoromethanesulfonate promoted atom-transfer additions of 3–bromoacetyl-2-oxazolidinone to several cycloalkenes proceeded smoothly to give functionalised cycloalkane derivatives in good yields and stereoselectivities. All products were easily and cleanly debrominated with tri(trimethylsilyl)silane to the corresponding stable cycloalkylacetic acid derivatives.
References
1.
(a)
Kharasch M.S.
,
Jensen E. V.
, and
Urry W. H
, Science , 1945 , 102 , 128 .
2.
Walling C.
, Free Radicals in Solution , Wiley and Sons : New York , 1957 , p. 252 .
3.
(a)
Curran D.P.
, Synthesis , 1988 , 489 .
4.
Curran D.P.
,
Bosch E.
,
Kaplan J.
, and
Newcomb M.
, J. Org. Chem. , 1989 , 54 , 1826 .
5.
Curran D.P.
,
Chen M. H.
,
Spletzer E.
,
Seong C. M.
, and
Chang C.
, J. Am. Chem. Soc. , 1989 , 111 , 8872 .
6.
(a)
Merro C.L.
, and
Porter N. A.
, J. Am. Chem. Soc. , 1999 , 121 , 5155 .
7.
Feng H.
,
Kavrakova I. K.
,
Pratt D. A.
,
Tellinghuisen J.
, and
Porter N. A.
, J. Org. Chem. , 2002 , 67 , 6050 .
8.
Gale L.H.
, J. Org. Chem. , 1968 , 33 , 3643 .
9.
Gale L.H.
, J. Org. Chem. , 1969 , 34 , 81 .
10.
Davies D.I.
,
Parfitt L. T.
,
Alden C. K.
, and
Claisse J. A.
, J. Chem. Soc.(C) , 1969 , 1585 .
11.
Osborn C.L.
,
Van Auken T. V.
, and
Trecker D. J.
, J. Am. Chem. Soc. , 1968 , 90 , 5806 .
12.
Narasaka K.
,
Hayashi Y.
,
Shimada S.
, and
Yamada J.
, Izr. J. Chem. , 1991 , 31 , 261 .