Abstract
It has been found by serendipity during the attempted synthesis of the potential tris-bidentate ligand 7 that this compound undergoes multiple ring-closure reactions to form the heterodamantane derivative 12. This reaction involves a domino aldol addition/hemiketal formation/hemiketal formation/epimerization sequence. Compound 12 was studied intensively by X-ray crystal-structure analysis, NMR, and AM1 computations. Complete assignment of all 1H- and 13C-NMR signals was achieved by a combination of HMQC, HMBC, DPFGSE-NOE, COSY, and long-range-COSY experiments. The NMR data agreed well with the crystallographic and computational results. Accordingly, 12 is present as the thermodynamically most-stable diastereoisomer with relative u-configuration at centers C(8) and C(9). In summary, five stereogenic centers were created starting from an achiral precursor in an efficient cascade reaction under thermodynamic control.
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