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5 coupling constants for the major diastereomers were smaller (usually in the 4.8-5.8 Hz range) than for the minor diastereomer typically in the 6.5-8.0 Hz range). The same trends were observed in the vinylogous Mannich products for which X-ray crystal structures are not available, thereby allowing attribution of their relative stereochemistry.
-
5 coupling constants for the major diastereomers were smaller (usually in the 4.8-5.8 Hz range) than for the minor diastereomer (typically in the 6.5-8.0 Hz range). The same trends were observed in the vinylogous Mannich products for which X-ray crystal structures are not available, thereby allowing attribution of their relative stereochemistry.
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46
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70349153681
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While the absolute configuration of the major isomer of compound 5h has not yet been, determined with, certainty, the observation by Ohsawa (ref 7a) that the (S)-valine-derived chiral auxiliary gives the Mannich product having the R configuration at d of isoquinoline combined with our observation that the major product formed in the vinylogous Mannich reaction has the R*,R* configuration strongly suggests that 5h therefore has the R,R configuration
-
While the absolute configuration of the major isomer of compound 5h has not yet been, determined with, certainty, the observation by Ohsawa (ref 7a) that the (S)-valine-derived chiral auxiliary gives the Mannich product having the R configuration at d of isoquinoline combined with our observation that the major product formed in the vinylogous Mannich reaction has the R*,R* configuration strongly suggests that 5h therefore has the R,R configuration.
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47
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70349154063
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γ of Si precludes use of the technique of ref 15 for attribution of the relative configuration
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γ of Si precludes use of the technique of ref 15 for attribution of the relative configuration.
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An attempt to rationalize the diastereoselectivity observed in the vinylogous Mannich reaction between 2-methoxyfuran and an N-carbamoylpyrrolinium salt has been reported. See: Bur, S. K.; Martin, S. F.
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