Highly enantioselective enzymatic resolution of aromatic β-amino acid amides with Pd-catalyzed racemization |
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Authors: | Eunjeong Choi Yunwoong Kim Yangsoo Ahn Jaiwook Park Mahn-Joo Kim |
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Institution: | Department of Chemistry, Pohang University of Science and Technology, San-31, Hyojadong, Pohang 790-784, Republic of Korea |
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Abstract: | The kinetic resolution of an aromatic β-amino acid amide 3a–d via N-acylation was explored with two lipases, Candida antarctica lipase A (CALA) and Pseudomonas stutzeri lipase (PSL). The PSL-catalyzed resolution proceeded with excellent enantioselectivity (E = >400) to give both acylated products and unreacted substrates in enantiopure forms. Three additional aromatic β-amino acid amides 3b–d were also resolved by PSL with a high level of enantioselectivity (E = >200). The PSL-catalyzed resolution of 3a was coupled with a Pd-catalyzed racemization to obtain enantiopure N-acylated product (R)-4a (>99% ee) in high yield (90%). |
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