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SmI2-promoted tandem desulfurization and reductive coupling reactions of aromatic lactams with carbonyl compounds

โœ Scribed by Hidemi Yoda; Yasuaki Ujihara; Kunihiko Takabe

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
87 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Treatment of sulfur-substituted aromatic lactams with carbonyl compounds in the presence of samarium(II) diiodide was found to undergo novel tandem desulfurization and reductive coupling reactions to generate a-hydroxyalkylated lactams in high yield. Stereochemistry of the coupling products was researched and the results that decreasing the steric bulkiness of the N-substituents as well as raising the reaction temperature leads to an increase of the erythro-selectivity were observed. The mechanistic origins of this stereoselectivity are also briefly documented.

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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Novel and stereoselective methods for th
Novel and stereoselective methods for the preparation of aromatic lactams via reductive coupling reactions mediated by SmI2
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Samarium(II) diiodide-mediated reductive cross-coupling of N-alkylated phthalimides with carbonyl compounds is shown to afford hydroxylated ฮฑ-hydroxylactams. Ketoamides obtained by dehydration of these compounds through keto-enol tautomer isomerization were reduced with NaBH 4 in a completely stereo