Adriaenssens, L.V. and Hartley, R.C. (2007) β-amino acids to piperidinones by petasis methylenation and acid-induced cyclization. Journal of Organic Chemistry, 72 (26). pp. 10287-10290. ISSN 00223263
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| Item Type: | Article |
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| Item Status: | Live Archive |
Abstract
(Chemical Equation Presented) Ester-imine derivatives of β-amino acids were methylenated with dimethyltitanocene under microwave irradiation and the resulting enol ethers cyclized with Brönsted acid or triisopropylaluminium to give 2,6-syn-disubstituted piperidinones in good yield and diastereoselectivity. The method is analogous to the Petasis - Ferrier rearrangement of 1,3-dioxan-4-ones to give tetrahydropyranones. © 2007 American Chemical Society.
| Additional Information: | cited By 12 The final published version of this article can be accessed online at https://pubs.acs.org/doi/abs/10.1021/jo7019948 |
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| Keywords: | Diastereoselectivity, Petasis methylenation, Piperidinones, Triisopropylaluminium, Acidity, Cyclization, Methylation, Microwave irradiation, Stereoselectivity, Amino acids, 1,3 dioxan 4 one, aluminum derivative, beta amino acid, dihyprylone, dimethyltitanocene, piperidone derivative, pyran derivative, tetrahydropyranone, titanocene, triisopropylaluminium, unclassified drug, article, chemical reaction, petasis ferrier reaction, stereochemistry, substitution reaction, Acids, Aluminum, Amino Acids, Microwaves, Molecular Structure, Organometallic Compounds, Piperidines, Stereoisomerism |
| Subjects: | F Physical Sciences > F100 Chemistry |
| Divisions: | College of Science > School of Chemistry |
| ID Code: | 22746 |
| Deposited On: | 25 Jul 2018 10:47 |
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