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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 10
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Original Articles

Complete Diastereofacial Selective Cycloaddition of New Sulfinyl Dienophiles (Ss)-and (Rs)-(-)Menthyl α-(2-Methoxyphenylsulfoxyl)acylate with Anthracene Under Chelation Control

Tay-Yuan Chau Department of Chemistry, National Chung-Hsing University, Taichung, Taiwan, 40227, Republic of China
,
Hsaio-Chi Lin Department of Chemistry, National Chung-Hsing University, Taichung, Taiwan, 40227, Republic of China
&
Wenhao Hu Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chengdu, 610041
Pages 1867-1874 | Received 09 Aug 1995, Published online: 21 Aug 2006

References and Notes

  • Ronan , B. and Kagan , H. B. 1991 . Tetrahedron : Asymmetry , 2 : 75
  • Bonfand , E. , Gosselin , P. and Maignan , C. 1993 . Tetrahedron : Asymmetry , 4 : 1667
  • Takahashi , T. , Fujii , A. , Sugita , J. , Hagi , T. , Kitano , K. , Arai , Y. and Koizumi , T. 1991 . Tetrahedron : Asymmetry , 2 : 1379 – 1390 .
  • Bonfand , E. , Gosselin , P. and Maignan , C. 1992 . Tetrahetron Lett. , 33 : 2347
  • Aversa , M. C. , Bonaccorsi , P. , Giannetto , P. , Jafari , S. M.A. and Jones , D. N. 1992 . Tetrahetron : Asymmetry , 3 : 701
  • De Lucci , O. , Marchioro , C. , Lucchini , V. and Valle , G. 1986 . J. Org. Chem. , 51 : 1457
  • Adams , H. , Jones , D. N. , Aversa , M. C. , Bonaccorsi , P. and Giannetto , P. 1993 . Tetrahedron Lett. , 34 : 6481
  • Hiroi , K. , Umemura , M. and Fujisawa , A. 1992 . Tetrahedron Lett. , 33 : 7161
  • Arai , Y. , Kuwayama , S.-i. , Takeuchi , Y. and Koizumi , T. 1985 . Tetrahedron Lett. , 26 : 6205
  • Koizumi , T. , Arai , Y. and Takayama , H. 1987 . Tetrahedron Lett. , 28 : 3689
  • Similar conclusion was obtained by Jones, D.N. (see ref. 3a)
  • Crystal data for 7a (C34H38O4S): monoclinic, space group P21, a=12.993(6) b=18.070(4) c=13.245(4)A, β=105.93(3)°, V=299.3(17)A3, Z=4, Dc=1.205g cm−3, 3107 independent observed reflections, 702 refined parameters, Robs=0,0358.
  • Compared to the cycloaddition of 1 with anthracene which proceeded at r.t. for 51 hr. under the presence of ZnCl2 reported by Koizumi (see ref.4a).

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