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

ABSTRACT: 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.

SUBMITTER: Lohse AG

PROVIDER: S-EPMC2993829 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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

Lohse Andrew G AG Krenske Elizabeth H EH Antoline Jennifer E JE Houk K N KN Hsung Richard P RP

Organic letters 20101104 23

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. ...[more]

PMID: 21049917

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