157008-40-7Relevant articles and documents
Lipase-catalyzed kinetic resolution of trans-2,5-disubstituted pyrrolidine derivatives
Kawanami, Yasuhiro,Moriya, Hitoko,Goto, Yuka,Tsukao, Keiko,Hashimoto, Michihiro
, p. 565 - 570 (1996)
Enantioselective preparation of C2-symmetric (-)-(2S,5S)-N-benzyl-trans-2,5-bis(acetoxymethyl)pyrrolidine was carried out by the lipase-catalyzed hydrolysis of racemic diacetate. Organic co-solvent affected the enantioselectivity and 50% DMSO in the phosphate buffer was found to be the optimal solvent system. A possible active site model was also described.
Symmetry-Assisted Synthesis of C2-Symmetric trans-α,α'-Bis(hydroxymethyl)pyrrolidine and -piperidine Derivatives via Double Sharpless Asymmetric Dihydroxylation of αω-Terminal Dienes
Takahata, Hiroki,Takahashi, Seiki,Kouno, Shin-Ichi,Momose, Takefumi
, p. 2224 - 2231 (2007/10/03)
A new strategy has been developed for the synthesis of C2-symmetric trans-α,α'-bis(hydroxymethyl)pyrrolidine and piperidine derivatives 1-3 starting from symmetric αω-terminal dienes 4-6. The double-asymmetric dihydroxylation (AD) reaction of 4-6 gave C2-symmetric tetrols, which were converted in a four-step sequence to C2-symmetric azacycloalkanes 17,9, and 22, respectively. These azacycloalkanes were transformed into 1-3 in high enantiomeric excess (82% → 98%ee). The double AD reaction proved to cause enantiomeric enhancement, even though the asymmetric induction for the first AD reaction is moderate. In addition, it was observed that the chromatography on silica gel of several C2-symmetric azacycloalkanes (17, 20, and 22) of varying ee's resulted in marked enantiomeric fractionation.
A facile synthesis of optically active C2-symmetric 2,5-disubstituted pyrrolidines and other β,β′-dihydroxyamines
Koh, Kevin,Ben, Robert N.,Durst
, p. 375 - 378 (2007/10/02)
2,5-Dibromoadipic acid has been converted into the di-(R)-pantolactone ester of (S,S)-pyyrolidine-2,5-dicarboxylic acid in two steps. This compound serves as a precursor to C2-symmetric 2,5-disubstituted pyrrolidines. The synthesis of linear C