Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

Nomura, Hiroshi and Richards, Chris (2009) Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles. Organic Letters, 11 (13). pp. 2892-2895.

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Abstract

Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC6H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Related URLs:
Depositing User: Rachel Smith
Date Deposited: 29 Mar 2011 10:42
Last Modified: 21 Apr 2020 17:43
URI: https://ueaeprints.uea.ac.uk/id/eprint/27397
DOI: 10.1021/ol900880w

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