J. Ruzicka, B. Koutek, L. Streinz
Sep 10, 1999
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Influential Citations
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Journal
Tetrahedron-asymmetry
Abstract
Abstract All four stereoisomers of 4-methylheptan-3-ol were synthesized by a five-step route starting from 4-thianones. Key steps in the synthesis include: (a) reduction of 3-propyl-4-thianone to yield an easily separable isomeric mixture of cis - and trans -3-propyl-4-thianols; and (b) a highly efficient resolution of the particular cis / trans -isomers through a chromatographic separation of their respective esters with ( S )-chlorofluoroacetic acid. Subsequent hydrolysis and desulfurization gave the required compounds in 18% overall yield. All the stereoisomers are obtained with purities better than 90%.