Relative stereochemical determination of beta-hydroxycarbonyl compounds (aldol products) utilizing the J-based configuration analysis method

摘要

beta-Hydroxycarbonyl moieties (aldol products) are common features in a variety of molecular structures. Whether this structural motif is synthetically prepared or incorporated into a natural product, the determination of the anti or syn (threo and erythro, respectively) relationship between the alpha and beta centers using previously reported NMR methods has, up to this point, been unreliable. Here, we report a method to determine the relative configuration of aldol products through the combined use Of (3)J(HH) homonuclear and, (n)J(CH) long-range heteronuclear coupling constants in tandem with dipolar couplings in a manner related to the previously described J-based configuration analysis method. Copyright (C) 2003 John Wiley Sons, Ltd. [References: 39]