Chemoenzymatic preparation of enantiopure l-benzofuranyl- and l-benzo[b]thiophenyl alanines

Lipase mediated DKR followed by a chemical and an enzymatic hydrolytic step were combined for the synthesis of enantiopure l-benzofuranyl- and l-benzothienyl alanines.

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l-2-Amino-3-(benzofuran-2-yl)propanoic acidC11H11NO3[α]D20=-14.5 (c 1, CH3COOH)Ee >99% on Chirobiotic-Tag HPLC column

l-2-Amino-3-(benzo[b]thiophen-2-yl)propanoic acidC11H11NO2S[α]D20=-23.8 (c 1, CH3COOH)Ee >99% on Chirobiotic-Tag HPLC column

l-2-Amino-3-(benzofuran-3-yl)propanoic acidC11H11NO3[α]D20=-8.0 (c 1, CH3COOH)Ee >99% on Chirobiotic-Tag HPLC column

l-2-Amino-3-(benzo[b]thiophene-3-yl)propanoic acidC11H11NO2S[α]D20=-26.0 (c 1, CH3COOH)Ee >99% on Chirobiotic-Tag HPLC column