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Stereocontrolled Access to Quaternary Centers by Birch Reduction/Alkylation of Chiral Esters of Salicylic Acids.

Ryan A KozlowskiHanh T NguyenMichael E LehmanChristopher D Vanderwal
Published in: The Journal of organic chemistry (2023)
8-Phenylmenthol esters of salicylic acid derivatives undergo efficient Birch reduction and in situ diastereoselective alkylations to afford methoxycyclohexadienes bearing new quaternary stereogenic centers. The use of an ester-based auxiliary is a designed improvement over the use of prolinol-derived amides, which are expensive and often very difficult to cleave.
Keyphrases
  • capillary electrophoresis
  • mass spectrometry