Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides
Abstract
:Introduction
Results and Discussion
Conclusion
Experimental
General
N-Maleonyl-(S)-alanine ethyl ester 4a
Method B
N-Maleonyl-(S)-valine-ethyl ester 4b
Method B
N-Maleonyl-(S)-leucine-methyl ester 4c
Method A
Method B
Method C
N-Maleonyl-(S)-serine- ethyl ester 4d
Method A
N-Maleonyl-(S)-aspartic acid diethyl ester 4e
Method A
Method B
Method C
N-Maleonyl-(S)-tryptophane-methyl ester 4f
Method B
1,3-Dipolar cycloaddition of 2,4,6-trimethylphenylnitrile oxide to maleimide 4a-e
1,3-Dipolar cycloaddition of phenylnitrile oxide to maleimide 4c,e
Acknowledgement
References
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Compd. | Method A Yield (%) | Method B Yield (%) | Method C Yield (%) |
---|---|---|---|
4a | < 5 | 28 | < 5 |
4b | < 5 | 50 | < 5 |
4c | 24 | 44 | 49 |
4d | 16 | x | < 5 |
4e | 39 | 62 | 55 |
4f | x | 50 | Mst |
Compound | R | Z | Ar | Ratio endo / exo |
---|---|---|---|---|
4a | CH3 | Et | Mst | 75 : 25 |
4b | (CH3)2CH | Et | Mst | 70 : 30 |
4c | (CH3)2CHCH2 | Me | Mst | 64 : 36 |
4c | (CH3)2CHCH2 | Me | Ph | 59 : 41 |
4d | CH2OH | Et | Mst | 59 : 41 |
4e | CH2COOEt | Et | Mst | 71 : 29 |
4e | CH2COOEt | Et | Ph | 72 : 28 |
4f | 3-Indolylmethyl | Me | Mst | 60 : 40 |
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Ondrus, V.; Fisera, L. Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides. Molecules 1997, 2, 49-56. https://doi.org/10.3390/feb97p5
Ondrus V, Fisera L. Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides. Molecules. 1997; 2(2):49-56. https://doi.org/10.3390/feb97p5
Chicago/Turabian StyleOndrus, Vladimir, and Lubor Fisera. 1997. "Synthesis and 1,3-Dipolar Cycloaddition Reactions of Chiral Maleimides" Molecules 2, no. 2: 49-56. https://doi.org/10.3390/feb97p5