Abstract
Radical Lewis acid promoted annulation reaction of 2-bromopentenoyl-2-oxazolidinones with 1-hexene proceeded smoothly under mild conditions to give functionalised cyclopentane derivatives in good yield but with modest diastereoselectivity. Reductive debromination with tris(trimethylsilyl)silane, LiOOH hydrolysis and esterification provided cleanly the corresponding cyclopentaneacetic acid and its methyl ester.
References
1.
Reviews on cyclopentannulation: (a)
Paquette L.A.
, and
Doherty A. M.
, Polyquinane Chemistry , Springer-Verlag : NY , 1987 .
2.
Ramaiah M.
, Synthesis , 1984 , 529 .
3.
Danheiser R.L.
,
Gee S. K.
, and
Sard H.
, J. Am. Chem. Soc. , 1982 , 104 , 7670 .
4.
Curran D.P.
,
Chen M. H.
,
Spletzer E.
,
Seong C. M.
, and
Chang C. T.
, J. Am. Chem. Soc. , 1989 , 111 , 8872 .
5.
Curran D.P.
, and
Chang C. T.
, J. Org. Chem. , 1989 , 54 , 3140 .
6.
(a)
Curran D.P.
, and
Seong C. M.
, Tetrahedron , 1992 , 48 , 2157 ; (b) 2175.
7.
(a)
Merro C.L.
, and
Porter N. A.
, J. Am. Chem. Soc. , 1999 , 121 , 5155 .
8.
Feng H.
,
Kavrakova I. K.
,
Pratt D. A.
,
Tellinghuisen J.
, and
Porter N. A.
, J. Org. Chem. , 2002 , 67 , 6050 .
9.
Kavrakova I.K.
, and
Mills J. H.
, J. Chem. Res. , 2005 , 1 , 59 .
10.
Kavrakova I.K.
,
Denkova P. S.
, and
Nikolova R. P.
, Tetrahedron: Asymmetry , 2005 , 16 , 1085 .
11.
Beckwith A.L. J.
, and
Schiesser C.
, Tetrahedron , 1985 , 41 , 3925 .
12.
Evans D.A.
,
Britton T. C.
,
Jonathan A. E.
, and
Dorow R. L.
, J. Am. Chem. Soc. , 1990 , 112 , 4011 .