Unknown

Dataset Information

0

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

altmetric image

Publications

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]

Similar Datasets

| S-EPMC3174849 | biostudies-literature
| S-EPMC4448725 | biostudies-literature
| S-EPMC4179875 | biostudies-literature
| S-EPMC4184932 | biostudies-literature
| S-EPMC2840463 | biostudies-literature
| S-EPMC8694347 | biostudies-literature
| S-EPMC4018150 | biostudies-literature
| S-EPMC3529139 | biostudies-literature
| S-EPMC4142980 | biostudies-literature
| S-EPMC3644032 | biostudies-literature