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 |
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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, 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 |
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| 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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