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79958787314
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In ref 4 the diastereoselective formation of a γ-lactam was reported as shown below. However, we could not apply this strategy to asymmetric synthesis because the reaction resulted in a complete racemization
-
In ref 4 the diastereoselective formation of a γ-lactam was reported as shown below. However, we could not apply this strategy to asymmetric synthesis because the reaction resulted in a complete racemization.
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79958848835
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The structure of 7a was determined by an X-ray crystallographic study
-
The structure of 7a was determined by an X-ray crystallographic study.
-
-
-
-
33
-
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79958785186
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3OD (1:1)
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3OD (1:1).
-
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36
-
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79958839357
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According to ref 3b, addition of the cyclohexenylzinc reagent gave poor selectivity when the lactam moiety was protected as its ethyl imidate. Thus protection of the nitrogen atom was essential to obtain the desired stereochemistry. We also tried introducing the cyclohexenyl moiety to the unprotected lactam by diastereoselective allylation followed by ring closing metathesis. In this case, the product turned out to be exclusively the undesired isomer
-
According to ref 3b, addition of the cyclohexenylzinc reagent gave poor selectivity when the lactam moiety was protected as its ethyl imidate. Thus protection of the nitrogen atom was essential to obtain the desired stereochemistry. We also tried introducing the cyclohexenyl moiety to the unprotected lactam by diastereoselective allylation followed by ring closing metathesis. In this case, the product turned out to be exclusively the undesired isomer.
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