A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential alpha-aminoxylation/ alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5-phenylpentan-2-ol, is also accomplished.
A general organocatalytic strategy for asymmetric synthesis of both syn/anti-1,3-diamines has been developed. The strategy employs proline-catalyzed sequential α-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step where syn-1,3-diamine was obtained as the most favorable product.
Biaryl‐substituted monophosphine‐based ligands have been synthesized by transition‐metal‐free “ARYNE” cross‐coupling reaction of aryllithiums with 1,2‐dibromobenzene and subsequent regioselective functionalization through bromine–lithium interconversion. These ligands were employed in palladium‐catalyzed C–N bond‐forming reactions. The reaction was found to be general with wide substrate applicability. A wide variety of both primary and secondary amines were successfully coupled with an array of differently substituted halobenzenes under microwave irradiation to give the expected products in good to excellent yields. A number of biaryl‐substituted phosphine ligands screened for the coupling reaction showed that steric bulk and the electronic properties of substituents on phosphorus play a crucial role in governing the catalytic activity of C–N cross‐coupling reactions.
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