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Title
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Stereoselective synthesis of functionalized bicyclic scaffolds by passerini 3-center-2-component reactions of cyclic ketoacids
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Author
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Abstract
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| We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product - the alpha-carboxamido lactone - into an atypical product, an alpha-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis. |
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Language
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English
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Source (journal)
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European journal of organic chemistry. - Weinheim, 1998, currens
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Publication
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Weinheim
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2017
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ISSN
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1434-193X
[print]
1099-0690
[online]
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DOI
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10.1002/EJOC.201601432
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Volume/pages
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9
(2017)
, p. 1262-1271
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ISI
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000395788100003
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Full text (Publisher's DOI)
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Full text (open access)
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