Tetrahedron: Asymmetry

Short syntheses of (S)-pipecolic acid,(R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

F Sánchez-Sancho, B Herradón

Index: Sanchez-Sancho, Francisco; Herradon, Bernardo Tetrahedron Asymmetry, 1998 , vol. 9, # 11 p. 1951 - 1965

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Citation Number: 74

Abstract

The kinetic resolutions of both (±)-N-(benzyloxycarbonyl-2-(hydroxymethyl) piperidine [(±)-5] and (±)-N-(tert-butoxycarbonyl)-2-(hydroxymethyl) piperidine [(±)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)-6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2–4 steps) and proceeded with ...