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 |
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| 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 |
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| Subjects: | F Physical Sciences > F100 Chemistry |
| Divisions: | College of Science > School of Chemistry |
| Related URLs: | |
| ID Code: | 19980 |
| Deposited On: | 11 Jan 2016 22:12 |
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