Tandem conjugate addition ireland claisen rearrangment
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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

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:

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


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: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.




More fast

Synlett. 1994, 271


Proposed Conjugate Addition/[3,3]-Rearrangement

TMSCl is need for high yield

J. Org. Chem. 2008, 73, 1575



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


2

3

J. Org. Chem. 1996, 61, 8728




DABCO is more better than Et3N, i-Pr2NEt, DMAP, PPh3

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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