Diastereoselective intramolecular photochemical [2 + 2] cycloaddition reactions of tethered l-(+)-valinol derived tetrahydrophthalimides

(Note: The full text of this document is currently only available in the PDF Version )

Kevin I. Booker-Milburn, Sirin Gulten and Andrew Sharpe


Abstract

Intramolecular photochemical [2 + 2] cycloaddition of allyl alcohol linked to amino acid derived 3,4,5,6-tetrahydrophthalimides, either via a carbonate or silicon tether, gives the corresponding cyclobutanes in excellent yield with diastereoselectivities as high as 8:1.


References

  1. B. S. Green, Y. Rabinsohn and M. Rejtö, Carbohydr. Res., 1975, 45, 115 CrossRef CAS; B. S. Green, A. T. Hagler, Y. Rabinsohn and M. Rejtö, Isr. J. Chem., 1976/77, 15, 124 Search PubMed; G. L. Lange, C. Decicco and M. Lee, Tetrahedron Lett., 1987, 28, 2833 CrossRef CAS; A. I. Meyers and S. A. Fleming, J. Am. Chem. Soc., 1986, 108, 306 CrossRef CAS; H. Herzog, H. D. Koch, H. D. Scharf and J. Runsink, Tetrahedron, 1986, 42, 3547 CrossRef CAS; M. Demuth, A. Palomer, H. D. Sluma, A. K. Dey, C. Kruger and Y. H. Tsay, Angew. Chem., Int. Ed. Engl., 1986, 25, 1117 CrossRef; M. Sato, K. Takayama, Y. Abe, T. Furuya, N. Inukai and C. Kaneko, Chem. Pharm. Bull., 1990, 38, 336 CAS; D. Haag and H. D. Scharf, J. Org. Chem., 1966, 61, 6127 CrossRef CAS; M. T. Crimmins and T. L. Reinhold, Org. React., 1993, 44, 297 CAS.
  2. S. A. Fleming and S. C. Ward, Tetrahedron Lett., 1992, 33, 1013 CrossRef CAS; C. L. Bradford, S. A. Fleming and S. C. Ward, Tetrahedron Lett., 1995, 36, 4189 CrossRef CAS.
  3. M. T. Crimmins and L. E. Guise, Tetrahedron Lett., 1994, 35, 1657 CrossRef CAS.
  4. S. Faure, S. Piva-Le Blanc, O. Piva and J.-P. Pete, Tetrahedron Lett., 1997, 38, 1045 CrossRef CAS.
  5. K. I. Booker-Milburn, J. K. Cowell and L. J. Harris, Tetrahedron Lett., 1994, 35, 3883 CrossRef CAS; K. I. Booker-Milburn, F. Delgado Jiménez and A. Sharpe, Synlett, 1995, 735 CrossRef CAS; K. I. Booker-Milburn, J. K. Cowell, A. Sharpe and F. Delgad Jiménez, Chem. Commun., 1996, 249 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.