Elsevier

Tetrahedron Letters

Volume 35, Issue 33, 15 August 1994, Pages 6047-6050
Tetrahedron Letters

PPL-catalyzed enzymatic asymmetrization of a 2-substituted prochiral 1,3-diol with remote chiral functionality: Improvements toward synthesis of the eutomers of SCH 45012

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Abstract

Porcine pancreatic lipase (PPL) catalysis has been used to establish both stereocenters of the cis-(tetrahydrofuranylmethy) tosylate 4. In addition to the enzymatic differentiation of the hydroxyl groups of the pro-chiral 1,3-diol segment of 2, successful enzymatic resolution of the racemic diol 10 provided an alternate route to the important precursor 1.

PPL lipase has been used to establish both stereocenters of intermediate 4, used in SCH 50001 and 50002 synthesis.

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