Abstract
The stereospecific aminocyclopropanation of styrene via the dethiolation of N,N-disubstituted aromatic thioamides promoted by the samarium/samarium diiodide mixed reagent has been successfully performed.
References
1.
For reviews of samarium diiodide, see: (a)
Curran D.P.
,
Jasperse C. P.
, and
Totleben M. J.
, Synlett , 1992 , 943 .
2.
Molander G.A.
, Chem. Rev. , 1992 , 92 , 29 .
3.
Molander G.A.
, and
Harris C. R.
, Chem. Rev. , 1996 , 96 , 29 .
4.
Molander G.A
, and
Harris C. R.
, Tetrahedron , 1998 , 54 , 3321 .
5.
Molander G.A.
, Acc. Chem. Res. , 1998 , 31 , 603 .
6.
Krief A.
, and
Laval A. M.
, Chem. Rev. , 1999 , 99 , 745 .
7.
Kagan H.B.
, Tetrahedron , 2003 , 59 , 10351 .
8.
(a)
Ogawa A.
,
Takami N.
,
Sekiguchi M.
,
Ryu I.
,
Kambe N.
, and
Sonoda N.
, J. Am. Chem. Soc. , 1992 , 114 , 8729 .
9.
Ogawa A.
,
Nanke T.
,
Takami N.
,
Sekiguchi M.
,
Ryu I.
,
Kambe N.
, and
Sonoda N.
, Appl. Organomet. Chem. , 1995 , 9 , 461 .
10.
(a)
Moss R.A.
,
Cox D. P.
, and
Tomioka H.
, Tetrahedron Lett. , 1984 , 25 , 1023 .
11.
Eisch J.J.
,
McNulty J. F.
, and
Shi X.
, J. Org. Chem. , 1994 , 59 , 7 .
12.
Ogawa A.
,
Takami N.
,
Nanke T.
,
Ohya S.
, and
Hirao T.
, Tetrahedron , 1997 , 53 , 12895 .
13.
Xu X.L.
, and
Zhang Y. M.
, Tetrahedron , 2002 , 58 , 503 .
14.
Poupaert J.H.
,
Bouinidane K.
,
Renard M.
,
Lambert D. M.
, and
Isa M.
, Organic Preparations and Procedures Int. , 2001 , 33 , 335 .
15.
Inanaga J.
,
Handa Y.
,
Tabuchi T.
,
Otsubo K.
,
Yamaguchi M.
, and
Hanamoyo T.
, Tetrahedron Lett. , 1991 , 32 , 6557 .
16.
Fischer E.O.
, Angew. Chem. , 1974 , 86 , 651 .
17.
Mills O.S.
, and
Redhouse A. D.
, J. Chem. Soc. A. , 1968 , 642 .
18.
Taylor T.E.
, and
Hall M. B.
, J. Am. Chem. Soc. , 1984 , 106 , 1576 ; H.M.L. Davies, P.R. Bruzinski, D. H. Lake, N. Kong and M.J. Fall, J. Am. Chem. Soc. , 1996, 118 , 6897.