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Asymmetric synthesis of 2-(hydroxyalkyl)-1,3-dithianes was achieved in good yields of up to 81% by using various 1,3-dithian-2-yl-substituted aliphatic aldehydes as substrates in the catalytic enantioselective addition of diethylzinc. With fair enantiomeric ratios of up to 85:15 in the enantiocontrolled ethylation step this synthetic approach provides an entry towards potential chiral building blocks.
The catalytic enantioselective ethylation of 3-(1,3-dioxolan-2-yl)-propanal by diethylzinc in the presence of various β-aminoalcohol precatalysts is presented. The enantiocontrolled alkylation step was accomplished with enantiomeric ratios of up to 86:14 and chemical yields ranging from 38 to 81% for the resulting 1-(1,3-dioxolan-2-yl)-3-pentanol.
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