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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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, 2006.

Additional Information:cited By 23 The final published version of this article can be accessed online at https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200600744 Copyright © 2006 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords:chemistry
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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