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Table 1 Identification of biocatalyst for the resolution of rac -3

From: Chemoenzymatic construction of chiral alkenyl acetylenic alcohol, a key building block to access diastereoisomers of polyacetylenes

Entry Biocatalyst Time (h) Conversion (%) a ( R )-3 b ( S )-11 b E c
% e.e. % e.e.
1 Lipase AK 0.5 >99 0 0 --
2 Novozym 435 0.5 56 96 97 340
3 Lipase PS 27.5 76 98 32 7
  1. Reaction conditions: rac-3 (151 mg, 0.5 mmol), biocatalyst (250 mg, 165% w/w), vinyl acetate (307 μL, 6.6 equiv), n-hexane (5 mL), R.T. aConversion was determined by HPLC (Chiralcel AS-H; flow rate: 0.50 mL/min; iPrOH/n-hexane: 1/99; temperature: 25°C; UV: λ = 199 nm); bthe determination of enantiomeric excess (HPLC chiralcel AS-H) and the absolute configuration (Mosher ester) of 3 are illustrated in Additional file 1; c E = ln[(1 − e.e.S)(1 − C)]/ln[(1 + e.e.S)(1 − C)], where e.e.S represents the enantiomeric excess of the recovered alcohol.