Enzymatic desymmetrization of pyrrolidine and pyrroline derivatives

The enzymatic desymmetrization of various meso-N-Boc-2,5-cis-disubstituted pyrrolidines and pyrrolines compounds by ester hydrolysis or transesterification provided the corresponding monoesters in high enantiomeric excess.

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tert-Butyl (3aR,4R,6S,6aS)-4-(acetoxymethyl)-6-(hydroxymethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylateC16H27NO7Ee = 97% (Chiral HPLC)[α]D20=-38.2 (c 1.20, CHCl3)Source of chirality: enzymatic desymmetrizationAbsolute configuration: (3aR,4R,6S,6aS)

tert-Butyl (2R,3R,4S,5S)-2-(acetoxymethyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine-1-carboxylateC13H23NO5Ee = 94%[α]D20=-8.7 (c 1.50, CHCl3)Source of chirality: enzymatic desymmetrizationAbsolute configuration: (2R,3R,4S,5S)

tert-Butyl (2S,5R)-2-(acetoxymethyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylateC13H23NO5Ee = 97% (Chiral GC)[α]D20=-10.9 (c 1.60, CHCl3)Source of chirality: enzymatic desymmetrizationAbsolute configuration: (2S,5R)

(2S,5R)-1-(tert-Butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidine-2-carboxylic acidC12H19NO6Ee ⩾ 98% (Chiral HPLC)[α]D20=+12.9 (c 1.40, MeOH)Source of chirality: enzymatic desymmetrizationAbsolute configuration: (2S,5R)