π-facial selectivities of diastereotopic ketones: P-bromobenzoates of 4-hetero-1-decalinols

Abstract

The crystal structures of the p-bromobenzoates of cis-4-oxa-1-decalinyl (C16H19BrO3), trans-4-oxa-1-decalinyl (C16H19BrO3), N-benzyl-cis-4-aza-1-decalinyl (C23H26BrNO2), N-benzyl-trans-4-aza-1-decalinyl (C23H26BrNO2) and trans-4-thia-1-decalinyl (C16H19BrO2S) (decalin is perhydronaphthalene) have been determined as part of a study directed at predicting and interpreting the π-facial selectivities of diastereotopic ketones in reactions with nucleophiles. All five structures are composed of molecules that are separated by normal van der Waals distances. In all five structures, the heterocyclic and cyclohexyl rings adopt chair conformations, and the p-bromobenzoate groups are planar.