Subtle Variations in the Long-Range Transmission of Stereochemical Information: Matched and Mismatched Aldol Reactions

Remote influences: The diastereofacial sense in which covalent bond formation is affected by remote stereogenic loci has been studied. An intermediate in the synthesis of the epothilones was the focus of these studies. Condensation of 1 and 2 gives rise to the single product in a “matched” aldol reaction. The transition states of the various reactions are discussed.