Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

Participants

Reaction Steps

Accordingly, diethyl benzylmalonate (1) is reduced with lithium aluminum hydride to afford 2-benzyl-1,3-propanediol (2) which is treated with an equimolar amount of tert-butyldimethylsilyl chloride to give the monoprotected alcohol 3. Swern (dimethylsulfoxide/oxalyl chloride) oxidation of 3 provides the aldehyde 4 which is condensed with the Wittig reagent methyl (triphenylphosphonylidene) acetate to give 6. Conversion of the alcohol 6 to the mesylate 7 followed by azide displacement affords 8 which is sequentially reduced and Boc protected to give 9. Jones oxidation of the tert-butyldimethylsilyl ether 9 provides the Boc protected substituted ω-aminoalkenoic acid 10.

Provenance & Evidence