124652-02-4Relevant academic research and scientific papers
Synthesis of Stereoisomeric 3-Substituted Cyclobutanecarboxylic Acid Derivatives
Dehmlow, Eckehard V.,Schmidt, Stefan
, p. 411 - 414 (2007/10/02)
The preparation of 3-substituted cyclobutanecarboxylic acids by ring forming malonic ester cycloalkylation/saponification/decarboxylation leads to 50:50 cis/trans mixtures.Only some polar ester derivatives 2 can be separated by chromatographic methods.Catalytic hydrogenation of 3-substituted cyclobutanecarboxylic acids 3, however, gives the cis acids 4 with 90-95 percent selectivity.Reduction of the same acids 3 by Zn in aqueous HCl/THF leads to the trans acids 6 with 90-93 percent selectivity.
