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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 3
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Original Articles

Stereoselective Construction of Functionalized, Trisubstituted (Z)-Allylsilanes and (Z)-Iodoalkenes

Pages 433-444 | Received 28 Jun 1995, Published online: 21 Aug 2006

References and Notes

  • Fish , P. V. 1994 . Tetrahedron Lett. , 35 : 7181
  • Brady , S. F. , Ilton , M. A. and Johnson , W. S. 1968 . J. Am. Chem. Soc. , 90 : 2882
  • Johnson , W. S. , Werthemann , L. , Bartlett , W. R. , Brocksom , T. J. , Li , T. -t. , Faulkner , D. J. and Petersen , M. R. 1970 . J. Am. Chem. Soc. , 92 : 741
  • Fish , P. V. , Reddy , P. S. , Lee , C. H. and Johnson , W. S. 1992 . Tetrahedron Lett. , 33 : 8001
  • Fish , P. V. and Johnson , W. S. 1994 . J. Org. Chem. , 59 : 2324 and references therein. These methods are compatible with polyene synthesis. For a recent example, see:
  • Fleming , I. 1991 . “ Allylsilanes, Allylstannanes and Related Systems ” . In Comprehensive Organic Synthesis , Edited by: Trost , B. M. and Fleming , I. Vol. 2 , pp 563 – 593 . Oxford : Pergamon Press . Methods of allylsilane formation:
  • Sarkar , T. M. 1990 . Synthesis , : 969 – 1101 .
  • Fleming , I. , Dunogues , J. and Smithers , R. 1989 . Organic Reactions , 37 : 57 – 575 .
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  • Casey , C. P. , Jones , C. R. and Tukada , H. 1981 . J. Org. Chem. , 46 : 2089 Note, μ-silyl α,β-unsaturated esters (e.g. 4) are thermally stable and do not undergo this rearrangement. For an example of the 1,5-migration of silicon from carbon to oxygen of a μ-silyl α,β-unsaturated ketone, see:
  • Negishi , E.-i. , Luo , F.-T. and Rand , C. L. 1982 . Tetrahedron Lett. , 23 : 27
  • Julia , M. , Julia , S. and Guegan , R. 1960 . Bull. Chim. Soc. Fr. , : 1072
  • Jacobi , P. A. , Kaczmarek , C. S.R. and Udodong , U. E. 1987 . Tetrahedron , 43 : 5475
  • Yukawa , Y. , Hanafusa , T. and Fujita , K. 1964 . Bull. Chem. Soc. Japan , 34 : 158
  • Marshall , J. A. , Lebreton , J. , DeHoff , B. S. and Jenson , T. M. 1987 . Tetrahedron Lett. , 28 : 723
  • Corey , E. J. , Katzenellenbogen , J. A. , Gilman , N. W. , Roman , S. A. and Erickson , B. W. 1968 . J. Am. Chem. Soc. , 90 : 5618
  • Brown , H. C. and Zweifel , G. 1961 . J. Am. Chem. Soc. , 83 : 1241
  • Zweifel , G. , Nagase , K. and Brown , H. C. 1962 . J. Am. Chem. Soc. , 84 : 190
  • Correspondence regarding this Article should be addressed to W. S. Johnson, Stanford University.

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