Regio- and Stereoselective Cascades via Aldol Condensation and 1,3-Dipolar Cycloaddition for Construction of Functional Pyrrolizidine Derivatives

An efficient and step-economical approach to access functionalized pyrrolizidine derivatives by a one-pot tandem sequence, including an aldol condensation and subsequent 1,3-dipolar cycloaddition process, has been developed, starting from acetone, aldehyde, and proline. A number of substituted aroma...

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Bibliographic Details
Published in:Organic letters 2018-02, Vol.20 (4), p.1090-1093
Main Authors: Mao, Zhuo-Ya, Liu, Yi-Wen, Han, Pan, Dong, Han-Qing, Si, Chang-Mei, Wei, Bang-Guo, Lin, Guo-Qiang
Format: Article
Language:English
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Summary:An efficient and step-economical approach to access functionalized pyrrolizidine derivatives by a one-pot tandem sequence, including an aldol condensation and subsequent 1,3-dipolar cycloaddition process, has been developed, starting from acetone, aldehyde, and proline. A number of substituted aromatic aldehydes were amenable to this transformation, and the desired products, racemic 7a–7w and chiral 9a–9m, were obtained with excellent regioselectivities and outstanding diastereoselectivities. Moreover, in situ NMR studies revealed MgSO4 could effectively promote the aldol condensation pathway in this tandem process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b04056