Subscribe to RSS
DOI: 10.1055/s-2002-34376
A Stereoselective and Regioselective Synthesis of trans,trans-Configured 1,2,3-Trisubstituted Indanes: Cycloaddition of Alkenes with Iodonium Ylides of β-Disulfones
Publication History
Publication Date:
26 September 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200214SpecialIssue/lookinside/thumbnails/10.1055-s-2002-34376-1.jpg)
Abstract
The reaction of phenyliodonium-bis(sulfonyl) methylides α-γ with alkenes 1 affords the multiply trisubstituted indanes 2 in moderate to good yields, through an unusual cycloaddition. The present stereoselective and regioselective cycloaddition provides a convenient preparative route to trans,trans-configured 1,2,3-trisubstituted indanes, in which the benzene ring derives from the arenesulfonyl functionality of the bis(sulfonyl)iodonium ylide. The mechanistically puzzling structural feature is the fact (X-ray structure) that the para-methyl substituent of the original p-toluenesulfonyl group in the iodonium ylide is located in the C-6 position of the resulting indane benzene ring, that is, a meta relationship with respect to the original methylide carbon atom.
Key words
cycloaddition - 1,2,3-trisubstituted indanes - iodonium ylides - diastereoselective synthesis
-
1a
Koser GF. In The Chemistry of Functional Groups, Supplement D Chap. 18: Wiley; New York: 1983. -
1b
Varvoglis A. The Organic Chemistry of Polycoordinated Iodine VCH; New York: 1992. -
1c
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997. -
1d
Moriarty RM.Vaid RK. Synthesis 1990, 431 -
2a
Hadjiarapoglou L.Varvoglis A.Alkock NW.Pike JA. J. Chem. Soc., Perkin Trans. 1 1988, 2839 -
2b
Hadjiarapoglou L.Spyroudis S.Varvoglis A. J. Am. Chem. Soc. 1985, 107: 7178 -
2c
Hadjiarapoglou LP. Ph.D. Thesis University of Thessaloniki; Greece: 1987. -
2d
Sander W.Strehl A.Winkler M. Eur. J. Org. Chem. 2001, 3771 - 3
Dieckman J. J. Org. Chem. 1965, 30: 2272 - For some recent examples on the synthesis of indanes, see:
-
4a
Kündig EP.Ratni H.Crousse B.Bernardinelli G. J. Org. Chem. 2001, 66: 1852 -
4b
Cordi AA.Berque-Bestel I.Persigand T.Lacoste J.-M.Newman-Tancredi A.Audinot V.Millan MJ. J. Med. Chem. 2001, 44: 787 -
4c
Kim S.Kitano Y.Tada M.Chiba K. Tetrahedron Lett. 2000, 41: 7079 -
4d
Ferraz HMC.Silva LF.Vieira TO. Tetrahedron 2001, 57: 1709 -
4e
Ferraz HMC.Silva LF. Tetrahedron 2001, 57: 9939 - 5
Simpkins NS. Sulphones in Organic Synthesis Pergamon; Exeter: 1993. -
6a
Moriarty RM.Prakash O.Vaid RK.Zhao L. J. Am. Chem. Soc. 1989, 111: 6443 -
6b
Moriarty RM.Prakash O.Vaid RK.Zhao L. J. Am. Chem. Soc. 1990, 112: 1297 -
6c
Moriarty RM.Kim J.Guo L. Tetrahedron Lett. 1993, 34: 4129 - 7
Farnia G.Sandonà G.Marcuzzi F.Melloni G. J. Chem. Soc., Perkin Trans. 2 1988, 247 -
8a
Clauss K. Chem. Ber. 1955, 88: 268 -
8b
Reich H.Cooperman C. J. Am. Chem. Soc. 1973, 95: 5077 -
9a
Wittig G.Rieber M. Liebigs Ann. Chem. 1949, 562: 187 -
9b
Beringer F.Chang L. J. Org. Chem. 1971, 36: 4055 -
10a
Trost BM.Schinsi WL.Chen F.Mantz IB. J. Am. Chem. Soc. 1971, 93: 676 -
10b
Padwa A.Gruber R. J. Org. Chem. 1970, 35: 1781 - 11
Stalke D. Chem. Soc. Rev. 1998, 27: 171 - 13
Sheldrick GM. SADABS 2.0 University of Göttingen; Germany: 2000. - 14
Sheldrick GM. Acta Crystallogr. 1990, 46A: 467 - 15
Sheldrick GM. SHELXL-97 University of Göttingen; Germany: 1997.
References
Bruker-AXS Inc.; SAINT-NT; Madison WI 2000.