Controlling diastereoselectivity in the tandem microwave-assisted aza-Cope rearrangement-Mannich cyclization

The first microwave-assisted version of the tandem aza-Cope rearrangement Mannich cyclization was developed. This sequence provides acylpyrrolidines in a single synthetic step while significantly reducing reaction times as compared to analogous reactions using conventional heating. Diastereoselectiv...

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Bibliographic Details
Published inSynlett no. 6; pp. 893 - 896
Main Authors Johnson, Benjamin F., Marrero, Edwin L., Turley, Wesley A., Lindsay, Harriet A.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.04.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cyclizations
CARBON BOND FORMATION
ORGANIC-SYNTHESIS
PYRROLIDINE
rearrangements
diastereoselectivity
amino alcohols
tandem reactions
STRATEGIES
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Summary:The first microwave-assisted version of the tandem aza-Cope rearrangement Mannich cyclization was developed. This sequence provides acylpyrrolidines in a single synthetic step while significantly reducing reaction times as compared to analogous reactions using conventional heating. Diastereoselectivity in these reactions may be improved by increasing the size of the amine-protecting group, an observation which has not been reported previously for aza-Cope-Mannich reactions leading to monosubstituted acylpyrrolidines. Finally, in some cases, diastereoselectivity could be improved by lowering the reaction temperature.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-973878