Journal
ORGANIC LETTERS
Volume 12, Issue 23, Pages 5506-5509Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1023745
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Funding
- NIH
- Australian Research Council [GM-36700, GM-66055, DP0985623]
- ARC Centre of Excellence for Free Radical Chemistry and Biotechnology
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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. OFT 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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