[3+2] Cycloaddition of Phenyliodonium Bis(arylsulfonyl)methylides with α,β-Enones

Waldemar Adam; Efstathios P. Gogonas; Ioannis A. Nyxas; Lazaros P. Hadjiarapoglou

doi:10.1055/s-2007-990801

PAPER

[3+2] Cycloaddition of Phenyliodonium Bis(arylsulfonyl)methylides with α,β-Enones

Waldemar Adam^a,b, Efstathios P. Gogonas^a,c, Ioannis A. Nyxas^c, Lazaros P. Hadjiarapoglou*^c
^a Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
^b Department of Chemistry, Facundo Bueso 110, University of Puerto Rico, Rio Piedras, Puerto Rico 00931, USA
^c Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
Fax: +30(26510)98799; e-Mail: lxatziar@uoi.gr;

Abstract

All articles of this category

Abstract

The [3+2] cycloaddition of phenyliodonium bis(arylsulfonyl)methylides to α,β-enones affords exclusively trans,trans-configured 1-(arylsulfonyl)-2-aroyl-3-arylindanes. The initial electrophilic attack of the iodonium ylide on the alkenyl double bond of the chalcone, followed by cyclization of the dipolar species, and subsequent ejection of iodobenzene and sulfur dioxide, stereoselectively affords the indane cycloadduct.

Key words

iodonium ylide - chalcones - diastereoselectivity - regioselectivity - 1,2,3-trisubstituted indanes

Full Text

References

1a Hadjiarapoglou L. Spyroudis S. Varvoglis A. J. Am. Chem. Soc. 1985, 107: 7178

1b Hadjiarapoglou L. Varvoglis A. Alcock NW. Pike GA. J. Chem. Soc., Perkin Trans. 1 1988, 2839

2a Hadjiarapoglou L. Varvoglis A. Synthesis 1988, 913

2b Hadjiarapoglou L. Varvoglis A. J. Heterocycl. Chem. 1988, 25: 1599

3 Adam W. Bosio S. Gogonas EP. Hadjiarapoglou LP. Synthesis 2002, 2084

4 Adam W. Gogonas EP. Hadjiarapoglou LP. J. Org. Chem. 2003, 68: 9155

5a Li AH. Dai L.-X. Aggarwal VK. Chem. Rev. 1997, 97: 2341

5b Barluenga J. Fanlo H. Lopez S. Florez J. Angew. Chem. Int. Ed. 2007, 46: 4136

6a Rozen S. Lerman O. Kol M. Hebel D. J. Org. Chem. 1985, 50: 4753

6b Jensen JL. Carre DJ. J. Org. Chem. 1974, 39: 2103

6c Adam W. Hadjiarapoglou L. Smerz A. Chem. Ber. 1991, 124: 227

7a Guziec FS. Luzzio FA. J. Org. Chem. 1983, 48: 2434

7b Jung ME. Min S.-J. Houk KN. Ess D. J. Org. Chem. 2004, 69: 9085

8 Simpkins NS. Sulphones in Organic Synthesis Pergamon; Exeter: 1993.

9a Rendy R. Zhamg Y. McElrea A. Gomez A. Klumpp DA. J. Org. Chem. 2004, 69: 2340

9b Minami K. Saito H. Tsutsui H. Nambu H. Anada M. Hashimoto S. Adv. Synth. Catal. 2005, 347: 1483

10 Sander W. Strehl A. Winkler M. Eur. J. Org. Chem. 2001, 3771

11a Reich HJ. Cooperman CS. J. Am. Chem. Soc. 1973, 95: 5077

11b Musher JI. J. Am. Chem. Soc. 1972, 94: 1370

12a Truce WE. Ray WJ. Norman OL. Eickemeyer DB. J. Am. Chem. Soc. 1958, 80: 3625

12b Truce WE. Robbins CR. Kreider EM. J. Am. Chem. Soc. 1966, 88: 4027

12c Madaj EJ. Snyder DM. Truce WE. J. Am. Chem. Soc. 1986, 108: 3466

13a Bergmann E. Wolff HA. J. Am. Chem. Soc. 1932, 54: 1644

13b Wheeler OH. Gore PH. Santiago M. Baez R. Can. J. Chem. 1964, 42: 2580

14 Palumbo G. Caputo R. Synthesis 1981, 888

15 Kohler EP. Tiechler M. J. Am. Chem. Soc. 1935, 57: 217