Enzymatic resolution of methyl (2E, 4R*,5S*)-4-(N-benzyl-N-methyl)amino-5-hydroxyhex-2-enoate

Add time:09/05/2019    Source:sciencedirect.com

For the purpose of preparation of optically active aminoalcohol congeners possessing both hydroxyl- and dialkylamino-substituted vicinal chiral carbons, lipase-assisted acylation of methyl (2E,4R*,5S*)-4-(N-benzyl-N-methyl)amino-5-hydroxyhex-2-enoate (4) using CAL-B with vinyl hexanoate as an acyl donor was carried out to give (4S,5R)-hexenoate (7) (44%, 99.2% ee) as the reaction product and (4R,5S)-alcohol (4) (46%, 98.2% ee) as the unreacted starting material. The E-value of the present lipase-assisted resolution was estimated to be more than 1000. Thus obtained acylated product was successfully converted into methyl β-d-vicenisaminide (12).

▶ The optically active amino-alcohol congener possessing hydroxyl and N,N-disubstituted amino groups with vicinal relationship are important building blocks for the synthesis of biologically and pharmacologically active compounds ▶ Lipase-assisted acylation of (±) methyl 4-(N-benzyl-N-methylamino)-5-hydroxy-2(E)-hexenoate using CAL-B with vinyl hexanoate as an acyl donor was carried out to give (4S,5R)-4-(N-benzyl-N-methylamino)-5-hexanoyloxy-2(E)-hexenoate (44%, 99.2% ee) and (4R,5S)-alcohol (46%, 98.2% ee) corresponding to starting material. ▶ The E-value of the present lipase-assisted resolution was estimated to be more than 1000. ▶ Thus obtained methyl (4S,5R)-4-(N-benzyl-N-methylamino)-5-hydroxy-2(E) hexenoate was successfully converted into methyl β-d-vicenisaminide.

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