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We have developed a practical synthesis of the chiral lactam as a new chiral building block for alkaloid synthesis. Lipase-catalyzed kinetic resolution of hydroxylactam 8, followed by isolation–racemization of the chiral acetoxylactam 9 provided the optically pure hydroxylactam 8 in 96.0% yield with >99% ee after five cycles of kinetic resolution–racemization process. Chemical transformation of...
High enantioselectivity was achieved in the lipase-catalyzed kinetic resolution of 5-hydroxypyrrolidin-2-one and 5-hydroxy-1,5-dihydropyrrol-2-one derivatives. Lipase PS and Novozym 435 were the successful catalysts (E=>1000). The acetylation of the N-protected 5-hydroxy-1,5-dihydropyrrol-2-one derivative gave the (R)-acetate with high enantioselectivity, while, without N-protection, the (S)-acetate...
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