Regioselectivities of (4 + 3) Cycloadditions between Furans and Oxazolidinone-Substituted Oxyallyls
- 4 November 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (23), 5506-5509
- https://doi.org/10.1021/ol1023745
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.Keywords
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