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All of the structures were optimized with no symmetry constraints, unless otherwise stated, and using the keyword PRECISE in order to meet rigorous criteria. In order to ensure that results did not involve an artifact, we used different geometries as starting structures in which all of the feasible conformations were considered (i.e. presence or absence of hydrogen bonding to the epoxy oxygen or oxazolinyl heteroatoms, steric hindrance). MOPAC 6.0: J. J. P. Stewart, QCPE 455, 1990. All of the calculations were performed using the keywords PM3, EF, and PRECISE.
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[25c] The syn (6) and anti (7) structures of the two diastereomeric chlorohydrins were determined by the ratios and structures of the (E)-(1j) and (Z)-oxazolinyl epoxides (1m), respectively.
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45
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