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

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CONTENTS  INTRODUCTION  REACTION  MECHANISM  APPLICATION  SCOPE  CONCLUSION  REFERENCE.

Presentation transcript:

张文全 tandem conjugate addition/ Ireland-Claisen rearrangment

Claisen rearrangement Eschemoser-Claisen rearrangement

Johnson-Claisen rearrangement Ireland-Claisen rearrangement

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

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

Methods of ketene acetal formation: 1.chemoselective deprotonation 2. electrochemical reduction Tetrohedron. Lett. 1992, 33, 3847

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

J. Org. Chem. 1993,58, 299

Condition A: PCy 3 (0.1 equiv), TESCl (3.0 equiv), DBU (2.6equiv), CHsCN, 50 o C, 24 h. Condition B: PCy 3 (0.05Sequiv), TMSCl(5.5 equiv), DBU (0.9 equiv), diisopropylethylamine (1.6 equiv), CH3CN, 80 O C, 24 h.

Tetrahedron lett. 1990, 31, 7457

Tetrahedron 1995, 51, 12631

Synlett. 1994, 271 More fast

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

For different treament after rearrangement:

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

J. Org. Chem. 1996, 61,

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

ORGANIC LETTERS 2007, 9, 1037

DABCO is more better than Et 3 N, i-Pr 2 NEt, DMAP, PPh 3 Only DBU can reaction too SYNLETT 2007, No. 2, 0288 Tetrahedron. 2007, 63, 9605

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

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