Synthesis of camphor-derived chiral auxiliaries and their application in asymmetric Morita-Baylis-Hillman reactions

Abstract

N-Substituted 2-exo-hydroxybornyl-10-sulfonamides, prepared as potential chiral auxiliaries for use in asymmetric Morita-Baylis-Hillman (MBH) reactions, have been treated with acryloyl chloride to afford the corresponding 2-exo-acrylate esters as MBH substrates. Reaction of selected 2-exo-acrylate ester substrates with pyridine-4-carbaldehyde and 6-methylpyridine-2-carbaldehyde in the presence of DABCO gave the expected MBH adducts in > 91% yield and with diastereoselectivities of 7-33% d.e.