Stereodivergent diversity oriented synthesis of piperidine alkaloids

Adriaenssens, L.V.a, Austin, C.A.a, Gibson, M.a , Smith, D.b and Hartley, R.C.a (2006) Stereodivergent diversity oriented synthesis of piperidine alkaloids. European Journal of Organic Chemistry, 2006 (22). pp. 4998-5001. ISSN 1434193X

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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, 2006.

Additional Information:cited By 23 The final published version of this article can be accessed online at Copyright © 2006 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:22747
Deposited On:25 Jul 2018 10:52

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