Synthesis and Diels-Alder reaction of novel C2-symmetric chiral dienes

The development and synthesis of a novel class of C2-symmetric outer ring dienes is described. Six novel chiral dienes, based upon the butane diacetal group, were synt4hsised from tartaric acid derivatives and the Diels-Alder reaction of three of these dienes was carried out. The diastereoselectivity of the Diels-Alder reaction with a range of dienophiles was investigated. The removal of the chiral auxiliary after the Diels-Alder reaction was also investigated. In an additional study tris-1,1,1-(hydroxymethyl)ethane was converted to a series of mono- and disubstituted derivatives. An indirect protocol, utilising chemoselective reactions, for the differentiation of the alcohol groups was employed for the synthesis of partially and fully differentiated tris-1,1,1-(hydroxymethyl)ethane containing a protected aldehyde unit.