trans-6-Aminocyclohept-3-enols, a New
Designed Polyfunctionalized Chiral
Building Block for the Asymmetric
Synthesis of
2-Substituted-4-hydroxypiperidines

Celestini, Paolo; Danieli, Bruno; Lesma, Giordano; Sacchetti, Alessandro; Silvani, Alessandra; Passarella, Daniele; Virdis, Andrea

doi:10.1021/ol025683x.s001

ol025683x_si_001.pdf (82.05 kB)

trans-6-Aminocyclohept-3-enols, a New Designed Polyfunctionalized Chiral Building Block for the Asymmetric Synthesis of 2-Substituted-4-hydroxypiperidines

journal contribution

posted on 2002-03-23, 00:00 authored by Paolo Celestini, Bruno Danieli, Giordano Lesma, Alessandro Sacchetti, Alessandra Silvani, Daniele Passarella, Andrea Virdis

trans-6-Aminocyclohept-3-enols 18 and ent-18 are new designed polyfunctionalized chiral building blocks for piperidine alkaloids synthesis and are prepared in high yields from the enzymatically derived cyclohept-3-ene-1,6-diol monoacetate (−)-8. Efficient highly enantioselective syntheses of cis-4-hydroxypipecolic acid (1) and piperidines 3 and 4, in both enantiomeric forms, are described.