Allylic Alkylations Catalyzed By Palladium-Bis(oxazoline) Complexes Derived From Heteroarylidene Malonate Derivatives
Abstract
:1. Introduction
2. Results and Discussion
Entry | Ligands | Solvent | Temp. (°C) | Time (h) | Yield b (%) | ee c (%) |
---|---|---|---|---|---|---|
1 | 4a | DCM | 20 | 24 | 85 | 92 |
2 | 4b | DCM | 20 | 24 | 85 | 90 |
3 | 4c | DCM | 20 | 24 | 80 | 47 |
4 | 5a | DCM | 20 | 24 | 90 | 91 |
5 | 5b | DCM | 20 | 24 | 86 | 89 |
6 | 5c | DCM | 20 | 24 | 80 | 15 |
7 | 4a | DCM | 0 | 48 | 80 | 96 |
8 | 4a | ClCH2CH2Cl | 0 | 48 | 85 | 84 |
9 | 4a | Toluene | 0 | 48 | 70 | 76 |
10 | 4a | CH3CN | 0 | 48 | 65 | 52 |
Entry | Substrates | Desired product a | Actual product b | ee c | |
---|---|---|---|---|---|
1 | | | | 5% | |
2 | | | | | 0 |
3 | | | | | 0 |
4 | | | | 0 | |
5 | | | | 0 | |
6 | | | | 0 | |
7 | | | | 0 |
3. Experimental
3.1. General
3.2. General Procedure for Catalytic Asymmetric Allylic Alkylation
(S-Dimethyl 2-[(E)-1,3-Diphenylprop-2-en-1-yl]malonate) (8)
3.3. Dimethyl 2-[(E)-1-methyl-3-phenylprop-2-en-1-yl]malonate (10)
3.4. Dimethyl 2-[(E)-1-phenylprop-2-en-1-yl]malonate (13)
3.5. Dimethyl 2-[(E)-3-naphthylprop-2-en-1-yl]malonate (16)
3.6. Dimethyl 2-[cyclohex-2-en-1-yl]malonate (18)
3.7. Dimethyl 2-[cyclopent-2-en-1-yl]malonate (20)
3.8. Methyl 2-carboxylate-2-cinnamyl 1-tetralone (23)
3.9. Methyl 2-carboxylate-2-allyl 1-tetralone (25)
4. Conclusions
Supplementary Materials
Acknowledgements
- Sample Availability: Samples of the compounds 10, 13, 16, 18, 20, 23 and 25 are available from the authors.
References and Notes
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Liu, L.; Ma, H.; Fu, B. Allylic Alkylations Catalyzed By Palladium-Bis(oxazoline) Complexes Derived From Heteroarylidene Malonate Derivatives. Molecules 2012, 17, 1992-1999. https://doi.org/10.3390/molecules17021992
Liu L, Ma H, Fu B. Allylic Alkylations Catalyzed By Palladium-Bis(oxazoline) Complexes Derived From Heteroarylidene Malonate Derivatives. Molecules. 2012; 17(2):1992-1999. https://doi.org/10.3390/molecules17021992
Chicago/Turabian StyleLiu, Lei, Hongli Ma, and Bin Fu. 2012. "Allylic Alkylations Catalyzed By Palladium-Bis(oxazoline) Complexes Derived From Heteroarylidene Malonate Derivatives" Molecules 17, no. 2: 1992-1999. https://doi.org/10.3390/molecules17021992