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New transformations of 2-nitro-2,3-dihydrofurans to multi-functionalized dihydrofurans

✍ Scribed by Jih Ru Hwu; Thota Sambaiah; Subhasish K. Chakraborty


Book ID
104253327
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
109 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis


A new type of transformation of 2-nitro-3-substituted-dihydrofurans to 4-formyl-2-hydroxy-3-substituted-2,3-dihydrofurans was accomplished in 63-84% yields by use of BF 3 β€’OEt 2 in CH 2 Cl 2 at -78 to 0Β°C.


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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 separat