Ontology highlight
ABSTRACT:
SUBMITTER: Lohse AG
PROVIDER: S-EPMC2993829 | biostudies-literature | 2010 Dec
REPOSITORIES: biostudies-literature
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]