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-h...

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Veröffentlicht in:	Organic letters 2002-04, Vol.4 (8), p.1367-1370
Hauptverfasser:	Celestini, Paolo, Danieli, Bruno, Lesma, Giordano, Sacchetti, Alessandro, Silvani, Alessandra, Passarella, Daniele, Virdis, Andrea
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids Cycloheptanes - chemical synthesis Heptanol - analogs & derivatives Heptanol - chemical synthesis Hydrogen-Ion Concentration Indicators and Reagents Lipase - chemistry Piperidines - chemical synthesis Stereoisomerism
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Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol025683x