Abstract
The synthesis of substituted 1-(2′-hydroxyphenyl)naphthalene-2-carbaldehydes 4 and 6-alkoxy-6H-pyrans 7 and 8, analogs of the postulated metallated intermediates in the atropo-enantioselective ring cleavage of configuratively unstable biaryl lactones 2, is described. While the equilibria between the open hydroxy aldehydes 4 and the cyclic lactol structures 3 are completely shifted towards 4 for the derivatives 4c-g with substituents ortho to the biaryl axis, the lactol forms are the dominating structures ( ca. 50–100%) for the ortho-unsubstituted compounds. For the lactols 3 and their acetalic analogs 6, 7, and 8, those diastereomeric conformations are preferred (77–100%) that have the exo-oxygen function axial.
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