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Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls

Regioselectivities of (4 + 3) cycloadditions between furans and oxazolidinone-substituted oxyallyls

Organic Letters 12(23): 5506-5509

The (4 + 3) cycloadditions of oxazolidinone-substituted oxyallyls and unsymmetrically substituted furans lead to syn regioselectivity when the furan has a 2-Me or 2-COOR substituent, while anti regioselectivity is obtained with a 3-Me or 3-COOR group. DFT calculations are performed to explain the selectivities. The reactivities and regioselectivities are consistent with the ambiphilic reactivity of amino-oxyallyls with furans.

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Accession: 055445929

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PMID: 21049917

DOI: 10.1021/ol1023745

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