Stereodivergent diversity oriented synthesis of piperidine alkaloids

Adriaenssens, Louis V., Austin, Carolyn A., Gibson, Mairi, Smith, David and Hartley, Richard C. (2006) Stereodivergent diversity oriented synthesis of piperidine alkaloids. European Journal of Organic Chemistry, 2006 (22). pp. 4998-5001. ISSN 1434-193X

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Item Type:Article
Item Status:Live Archive

Abstract

Alkylidenetitanium reagents enable the reagent-controlled high throughput asymmetric synthesis of 2-substituted piperidines and rapid access to multiple cyclic imines using solid phase synthesis (SPS). The Schrock carbenes, generated by reduction of thioacetals, convert resin-bound esters into enol ethers. Treatment with acid releases amino ketones that are cyclized with TMSCl to give iminium salts. Reduction introduces a chiral centre at C-2, whose absolute stereochemistry is determined by a phenethylamine (PEA) chiral auxiliary. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Keywords:Amines;Asymmetric synthesis;Combinatorial chemistry;Solid-phase synthesis;Titanium complexes
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
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ID Code:19980
Deposited On:11 Jan 2016 22:12

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