Abstract
Cyclopropane derivatives were synthesised in one pot from aromatic aldehydes, phenacyltriphenylphosphonium bromide, and S-phenacylthiolanium bromide by a Wittig olefination-sulfur ylide cyclopropanation sequence. When Cs2CO3 was used as the base and CH3CN/water (8:2, v/v) as the solvent, the major product was the cis-1,2-dibenzoyl cyclopropane. In contrast, when using DBU as the base and MeOH as the solvent, the major product was trans-dibenzoyl cyclopropane. In some cases, the major isomer was obtained in high purity and good yield by simple filtration.
References
1.
Wessjohann L.A.
, and
Brandt W.
, Chem. Rev. , 2003 , 103 , 1625 .
2.
de Meijere A.
, and
Kozhushkov S.I.
, Mendeleev Commun. , 2010 , 20 , 301 .
3.
Lebel H.
,
Marcoux J.-F.
,
Molinaro C.
, and
Charette A.B.
, Chem. Rev. , 2003 , 103 , 977 .
4.
Pellissier H.
, Tetrahedron , 2008 , 64 , 7041 .
5.
Riches S.I.
,
Saha C.
,
Filgueira N.F.
, et al., J. Am. Chem. Soc. , 2010 , 132 , 7626 .
6.
Aggarwal V.K.
, and
Grange E.
, Chem. Eur. J. , 2006 , 12 , 568 .
7.
Aggarwal V.K.
,
Charmant J.P.H.
,
Fuentes D.
, et al., J. Am. Chem. Soc. , 2006 , 128 , 2105 .
8.
Zhou R.
,
Deng X.
,
Zheng J.
,
Shen Q.
,
Sun X.
, and
Tang Y.
, Chin. J. Chem. , 2011 , 29 , 995 .
9.
Ilic D.
,
Damljanovic I.
,
Vukicevic M.
, et al., Tetrahedron Lett. , 2012 , 53 , 6018 .
10.
Janardanan D.
, and
Sunoj R.B.
, Org. Biomol. Chem. , 2011 , 9 , 1642 .
11.
Cheng Y.
,
An J.
,
Lu L.-Q.
, et al., J. Org. Chem. , 2011 , 76 , 281 .
12.
Deng X.-M.
,
Cai P.
,
Ye S.
, et al., J. Am. Chem. Soc. , 2006 , 128 , 9730 .
13.
Janardanan D.
, and
Sunoj R.B.
, J. Org. Chem. , 2007 , 72 , 331 .
14.
Maercker A.
, Org. React. , 1965 , 14 , 270 .
15.
Clarke P.A.
,
Santos S.
, and
Martin W.H.C.
, Green Chem. , 2007 , 9 , 438 .
16.
Oswald M.F.
,
Raw S.A.
, and
Taylor R.J.K.
, Org. Lett. , 2004 , 6 , 3997 .
17.
McAllister G.D.
,
Oswald M.F.
,
Paxton R.J.
, et al., Tetrahedron , 2006 , 62 , 6681 .
18.
Li A.-H.
,
Dai L.-X.
, and
Aggarwal V.K.
, Chem. Rev. , 1997 , 97 , 2341 .
19.
Corey E.J.
, and
Chaykovsky M.
, J. Am. Chem. Soc. , 1965 , 87 , 1353 .
20.
Aggarwal V.K.
, and
Hebach C.
, Org. Biomol. Chem. , 2005 , 3 , 1419 .
21.
Edwards D.R.
,
Du J.
, and
Crudden C.M.
, Org. Lett. , 2007 , 9 , 2397 .
22.
Edwards D.R.
,
Montoya-Peleaz P.
, and
Crudden C.M.
, Org. Lett. , 2007 , 9 , 5481 .
23.
Trost B.M.
, J. Am. Chem. Soc. , 1967 , 89 , 138 .
24.
Peppe C.
,
das Chagas R.P.
, and
Burrow R.A.
, J. Organomet. Chem. , 2008 , 693 , 3441 .
25.
El-Batta A.
,
Jiang C.
,
Zhao W.
, et al., J. Org. Chem. , 2007 , 72 , 5244 .
26.
Ramirez F.
, and
Dershowitz S.
, J. Org. Chem. , 1957 , 22 , 41 .
27.
Borredon M.E.
,
Delmas M.
, and
Gaset A.
, Tetrahedron , 1987 , 43 , 3945 .
28.
Fuglseth E.
,
Thvedt T.H.K.
,
Moll M.F.
, and
Hoff B.H.
, Tetrahedron , 2008 , 64 , 7318 .