trans-6-Aminocyclohept-3-enols, a new designed polyfunctionalized chiral building block for the asymmetric synthesis of 2-substituted-4-hydroxypiperidines.
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]
Celestini
Paolo
P
Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via Venezian 21, 20133 Milan, Italy.
Danieli
Bruno
B
Lesma
Giordano
G
Sacchetti
Alessandro
A
Silvani
Alessandra
A
Passarella
Daniele
D
Virdis
Andrea
A
D000470:Alkaloids; D003508:Cycloheptanes / Q000138:chemical synthesis*; D019850:Heptanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D008049:Lipase / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D003508:Cycloheptanes; D007202:Indicators and Reagents; D010880:Piperidines; D019850:Heptanol; D008049:Lipase