Aza Diels–Alder reactions utilizing 4-iodo-2-trimethylsilyloxy-butadiene

The aza Diels–Alder reaction is described for a novel diene. Imines bearing benzyl and aromatic protecting groups both work well. Moderate diastereoselectivities can be obtained using the simple α-methylbenzyl chiral auxiliary. Graphical Abstract

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Bibliographic Details
Published in:Tetrahedron 2005-12, Vol.61 (50), p.11837-11842
Main Authors: Timmons, Cody, Kattuboina, Adiseshu, McPherson, Lauren, Mills, James, Li, Guigen
Format: Article
Language:English
Subjects:
Aza Diels–Alder
Dihydropyridones
Magnesium iodide
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Description
Summary:The aza Diels–Alder reaction is described for a novel diene. Imines bearing benzyl and aromatic protecting groups both work well. Moderate diastereoselectivities can be obtained using the simple α-methylbenzyl chiral auxiliary. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.10.018