On the steric course of addition of 1-lithio- and 1-magnesio-2-pivaloyl-1,2,3,4-tetrahydroisoquinoline to aldehydes and ketones. An x-ray crystal structure determination of the organomagnesium reagent
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23
摘要：
The steric course of the diastereoselective addition of the 1-bromomagnesium derivative 2 of N-pivaloyl-tetrahydroisoquinoline (THIQ) to acetophenone is proved by X-ray crystal structure analysis of the major product 1-(α-hydroxy-α-methylbenzyl)-2-pivaloyl-1,2,3,4-tetrahydroisoquinoline (4) to be the same as that for aldehydes (relative topicity ul, configuration of the adducts u). The reaction is much less selective if the lithiated reagent is employed. The crystal structure of the magnesium reagent (2) was determined. As crystallized from THF, 2 is monomeric, with an octahedrally coordinated Mg with three THF oxygens, the THIQ carbon, the pivaloyl oxygen and a bromine as ligands. A mechanistic proposal derived from the crystal structure explains both the higher selectivity observed with the Mg derivative and the fact that the u-diastereomer is formed preferentially.
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DOI：
10.1016/0022-328X(85)87352-6
被引量：
年份：
1985
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