Abstract
A stereoselective synthesis of functionalized sulfonyl-substituted cycloheptanes is described. The approach involves a formal two-carbon ring expansion of 2-benzenesulfonyl cyclopentanones through a base-induced anionic domino three-component transformation named the MARDi cascade.
Key words
stereoselective synthesis - domino reactions - multi-component reactions - ring expansion - cycloheptane
References and Notes
1a Rodriguez J.
Synlett
1999,
505
1b Simon C.
Constantieux T.
Rodriguez J.
Eur. J. Org. Chem.
2004,
4957
1c Liéby-Muller F.
Simon C.
Constantieux T.
Rodriguez J.
QSAR Comb. Sci.
2006,
25:
432
2a Filippini M.-H.
Rodriguez J.
Santelli M.
J. Chem. Soc., Chem. Commun.
1993,
1647
2b Filippini M.-H.
Rodriguez J.
J. Org. Chem.
1997,
62:
3034
2c The structure of the cycloheptenic acids 3 has been reviewed and confirmed to be as depicted in Scheme
[1 A (Scheme
[3
3a Filippini M.-H.
Rodriguez J.
Chem. Rev.
1999,
99:
27
3b Filippini M.-H.
Faure R.
Rodriguez J.
J. Org. Chem.
1995,
60:
6872
4a Yet L.
Tetrahedron
1999,
55:
9349
4b Yet L.
Chem. Rev.
2000,
100:
2963
4c Kantorowski EJ.
Kurth MJ.
Tetrahedron
2000,
56:
4317
4d Maier ME.
Angew. Chem. Int. Ed.
2000,
39:
2073
4e Arjona O.
de Dios A.
Fernández de la Pradilla R.
Plumet J.
Viso A.
J. Org. Chem.
1994,
59:
3906
4f Arjona O.
Plumet J.
Curr. Org. Chem.
2002,
6:
571
4g El-Awa A.
Fuchs P.
Org. Lett.
2006,
8:
2905
5 Trost BM.
Salzmann TN.
Hiroi K.
J. Am. Chem. Soc.
1976,
98:
4887
6 Carreño MC.
García Ruano JL.
Pedregal C.
Rubio A.
J. Chem. Soc., Perkin Trans. 1
1989,
1335
7 Kraus GA.
Hansen J.
Vines D.
Synth. Commun.
1992,
22:
2625
8 Hashimoto N.
Aoyama T.
Shiori T.
Chem. Pharm. Bull.
1981,
29:
1475
9 Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, with CCDC numbers 615710, 615708, 615709 for com-pounds A , 8 and 9 , respectively. Copies of this information can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk or www: http://www.ccdc.cam.ac.uk].
