Substitution of one or both TADDOL OH groups by other functional groups X, Y is key to new applications of this cheap chiral auxiliary. The Appel reaction and treatment with SOCl 2 provide the mono- and dichlorides, respectively. The chlorides are, in turn, replaced by various nucleophiles, and further modifications give a large variety of derivatives, including mono- and ditritylated dioxolanes. The new compounds available in either enantiomeric form are ready to be used in enantioselective synthesis and as dopants in liquid crystals.
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Seebàch et al. (1999) studied this question.
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