A Novel Asymmetric Synthesis of Chiral Cyclopentanoid Building Blocks by the Use of Chiral Lithium Amide

Enantioselective deprotonation of meso-epoxides, derived from 3-cyclopenten-1-ol, was examined using chiral lithium amide. Chiral cis-4-t-butyldimethylsiloxy-2-cyclopenten-1-ol, cis-4-tetrahydropyranyloxy-2-cyclopenten-1-ol, and their trans-isomers, which are useful chiral building blocks for the synthesis of cyclopentanoid natural compounds, were obtained with high enantiomeric excesses (72–90% ee). Both (R)- and (S)-4-hydroxy-2-cyclopenten-1-one were derived from (1S,4R)-4-t-butyldimethylsiloxy-2-cyclopenten-1-ol stereospecifically.