200644-41-3Relevant academic research and scientific papers
Both enantiomers of N-Boc-indoline-2-carboxylic esters
Kurokawa, Masayuki,Sugai, Takeshi
, p. 1021 - 1025 (2004)
An immobilized form of Candida antarctica lipase (Chirazyme L-2) catalyzed enantioselective hydrolysis (E > 1000) of N-Boc-indoline-2-carboxylic acid methyl ester. The reaction proceeded efficiently at 60 °C, a temperature over the melting point of substrate, in the conversion of 49.9% to provide the hydrolyzed product, (S)-carboxylic acid with >99.9% ee and the unreacted (R)-ester with 99.6% ee. A newly developed expeditious route to the racemic substrate (a total of six steps, 60% yield), starting from aniline and ethyl α-methylacetoacetate, established the scalable chemoenzymatic synthesis of the desired compounds in both enantiomerically pure forms.
On the origins of enantioselectivity in oxazaborolidine mediated carbonyl reductions
Jones, Graham B.,Heaton, Steven B.,Chapman, Brant J.,Guzel, Mustafa
, p. 3625 - 3636 (2007/10/03)
A series of tricyclic oxazaborolidine catalysts have been prepared from readily available (S)-indoline-2-carboxylic acid. In each case, an arene chromium(0) carbonyl group was introduced on one face of the catalyst. Results obtained in the borane mediated
