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Asymmetric Mn(III)-based radical synthesis of functionalized 2,3-dihydrofurans

✍ Scribed by Frédéric Garzino; Alain Méou; Pierre Brun

Book ID: 104211276
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 78 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01729-9

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✦ Synopsis

The oxidative radical addition of alkyl acetoacetates to p-methoxycinnamoyl oxazolidinones promoted by Mn(III) has been studied. It only gives trans-disubstituted 2,3-dihydrofurans, with d.r. ranging from 2:1 to 9:1, depending on the substituent of the chiral auxiliary. After chromatographic separation of the two diastereomers, the oxazolidinone can be removed to afford enantiopure dihydrofuranyl esters in good overall yield.

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