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tandem conjugate addition/ Ireland-Claisen rearrangment

tandem conjugate addition/ Ireland-Claisen rearrangment. 张文全 2001. 6. 11. Claisen rearrangement. Eschemoser-Claisen rearrangement. Johnson-Claisen rearrangement. Ireland-Claisen rearrangement. History first. Tseou, H.-F.; Wang, Y.-T. J. Chin. Chem. Soc. 1937, 5, 224. Other:.

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tandem conjugate addition/ Ireland-Claisen rearrangment

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  1. tandem conjugate addition/Ireland-Claisen rearrangment 张文全 2001. 6. 11

  2. Claisen rearrangement Eschemoser-Claisen rearrangement

  3. Johnson-Claisen rearrangement Ireland-Claisen rearrangement

  4. History first Tseou, H.-F.; Wang, Y.-T. J. Chin. Chem. Soc. 1937, 5, 224 Other: J. Am. Chem. Soc. 1949, 71, 1150 J. Org. Chem. 1960, 25, 1815 Bull. Soc. Chim. Fr. 1964, 25, 2693

  5. Synth. Commun. 1972, 2, 21 LICA ：lithium isopropylcyclohexylamide Ireland. R. E. J. Am. Chem. Soc. 1972, 94, 5897

  6. Methods of ketene acetal formation: • chemoselective deprotonation 2. electrochemical reduction Tetrohedron. Lett. 1992, 33, 3847

  7. 3. Conjuate addition tandem conjugate addition/ireland-Claisen rearrangment

  8. J. Org. Chem. 1993,58, 299

  9. Condition A:PCy3 (0.1 equiv), TESCl (3.0equiv), DBU (2.6equiv), CHsCN, 50oC, 24 h. Condition B: PCy3 (0.05Sequiv), TMSCl(5.5equiv), DBU (0.9equiv), diisopropylethylamine (1.6equiv), CH3CN, 80 OC, 24h.

  10. Tetrahedron lett. 1990, 31, 7457

  11. Tetrahedron 1995, 51, 12631

  12. More fast Synlett. 1994, 271

  13. Proposed Conjugate Addition/[3,3]-Rearrangement TMSCl is need for high yield J. Org. Chem. 2008, 73, 1575

  14. For different treament after rearrangement:

  15. Addition of palladium dichloridebenzonitrile complex at the rearrangement step was found to effectively suppress the unfavorable formation of the side products J. Org. Chem. 1995,60, 8140

  16. 2 3 J. Org. Chem. 1996, 61, 8728

  17. J. AM. CHEM. SOC. 2005, 127, 2046

  18. ORGANIC LETTERS 2007, 9, 1037

  19. DABCO is more better than Et3N, i-Pr2NEt, DMAP, PPh3 Only DBU can reaction too SYNLETT 2007, No. 2, 0288 Tetrahedron. 2007, 63, 9605

  20. J. Am. Chem. SOC. 1991,113,4026

  21. thankyou for your attention

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