Synthesis of four diastereomeric 3,5-dialkoxy-2,4-dimethylalkanals by a simple extension of the non-aldol aldol process to bis(propionates).
[formula: see text] The synthesis of all four diastereomers of bis(propionates), 3,5-dialkoxy-2,4-dimethylalkanals, by non-aldol aldol chemistry is described. The epoxy alcohols (3, 4) were converted into the mesylates (9, 11) which were cleanly rearranged to the desired 3,5-bis(oxygenated)-2,4-dimethylalkanals (10, 12) in high yield. The epoxy mesylates (13, 16) gave the desired products (14, 17) in good yield on treatment with TMSOTf and a hindered base.
Jung
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Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA. jung@chem.ucla.edu
Lee
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Sun
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D
D000447:Aldehydes / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D017646:Organosilicon Compounds / Q000138:chemical synthesis*; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D004852:Epoxy Compounds; D008698:Mesylates; D017646:Organosilicon Compounds; D011422:Propionates