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, 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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container_end_page 1370
container_issue 8
container_start_page 1367
container_title Organic letters
container_volume 4
creator Celestini, Paolo
Danieli, Bruno
Lesma, Giordano
Sacchetti, Alessandro
Silvani, Alessandra
Passarella, Daniele
Virdis, Andrea
description 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.
doi_str_mv 10.1021/ol025683x
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source MEDLINE; ACS Publications
subjects Alkaloids
Cycloheptanes - chemical synthesis
Heptanol - analogs & derivatives
Heptanol - chemical synthesis
Hydrogen-Ion Concentration
Indicators and Reagents
Lipase - chemistry
Piperidines - chemical synthesis
Stereoisomerism
title trans-6-Aminocyclohept-3-enols, a New Designed Polyfunctionalized Chiral Building Block for the Asymmetric Synthesis of 2-Substituted-4-hydroxypiperidines
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