Diastereo- and Enantioselective Synthesis of syn- and anti-1,2-Diol Units by Asymmetric Aldol Reactions

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Abstract
syn- and anti-1,2-Diol units were prepared by using asymmetric aldol reactions of the silyl enol ethers derived from α-alkoxythioacetic S-esters with aldehydes. In the presence of tin(II) triflate, a chiral diamine, and dibutyltin diacetate, (Z)-2-benzyloxy-1-ethylthino-1-(trimethylsiloxy)ethene reacted with aldehydes to afford the corresponding anti-aldol adducts in high yields with excellent diastereo- and enantioselectivities, while syn-adducts were obtained from (Z)-2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene and aldehydes under the same reaction conditions. Thus, both diastereomers can be synthesized in excellent enantiomeric excesses by simply choosing the protective groups of the alkoxyl parts of the silyl enol ethers.