108864-34-2Relevant articles and documents
Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a "Capture and Release" Strategy
Humphrey, Cara E.,Turner, Nicholas J.,Easson, Morag A. M.,Flitsch, Sabine L.,Ulijn, Rein V.
, p. 13952 - 13953 (2003)
The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(?)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin. Copyright
Solid-supported cyclohexane-1,3-dione (CHD): A "capture and release" reagent for the synthesis of amides and novel scavenger resin
Humphrey, Cara E.,Easson, Morag A. M.,Tierney, Jason P.,Turner, Nicholas J.
, p. 849 - 852 (2007/10/03)
A three-step synthesis of cyclohexane-1,3-dione (CHD) resin 6 on polystyrene resin is described. Resin 6 was used to prepare an amide library of high purity by microwave-assisted serial "capture and release" and can be recycled for this purpose. High-loading CHD resin 10 was also shown to scavenge allyl cations in solution.
Preparation of Some 1-Alkyl-4-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic Acid Ester and Amide Herbicides by Reductive Alkylation of 3,5-Dimethioxybenzoic Acid
Liepa, Andris J.,Wilkie, John S.,Winzenberg, Kevin N.
, p. 1217 - 1225 (2007/10/02)
Reductive alkylation of 3,5-dimethoxybenzoic acid with haloalkanes afforded the 1-alkyl-3,5-dimethoxycyclohexa-2,5-diene-1-carboxylic acid derivatives (3a-e) which, upon esterification and hydrolysis furnished methyl 1-alkyl-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (4f-j).Reaction of (4f-j) with butyric anhydride gave methyl 1-alkyl-4-butyryl-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-e) which were converted into methyl 1-alkyl-4--3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (2a-e).Similarly, the oximeO-ether derivative (2f) was prepared from the amide (4l), obtained from reaction of (3b) with N,N'-carbonyldiimidazole and dimethylamine followed by hydrolysis.
