trans-6-Aminocyclohept-3-enols, a new designed polyfunctionalized chiral building block for the asymmetric synthesis of 2-substituted-4-hydroxypiperidines

Org Lett. 2002 Apr 18;4(8):1367-70. doi: 10.1021/ol025683x.

Abstract

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. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids
  • Cycloheptanes / chemical synthesis*
  • Heptanol / analogs & derivatives*
  • Heptanol / chemical synthesis
  • Hydrogen-Ion Concentration*
  • Indicators and Reagents
  • Lipase / chemistry
  • Piperidines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Cycloheptanes
  • Indicators and Reagents
  • Piperidines
  • Heptanol
  • Lipase