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

Lohse, Andrew G., Krenske, Elizabeth H., Antoline, Jennifer E., Houk, K. N. and Hsung, Richard P. (2010) Regioselectivities of (4+3) cycloadditions between furans and oxazolidinone-substituted oxyallyls. Organic Letters, 12 23: 5506-5509. doi:10.1021/ol1023745


Author Lohse, Andrew G.
Krenske, Elizabeth H.
Antoline, Jennifer E.
Houk, K. N.
Hsung, Richard P.
Title Regioselectivities of (4+3) cycloadditions between furans and oxazolidinone-substituted oxyallyls
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
1523-7052
Publication date 2010-12
Sub-type Article (original research)
DOI 10.1021/ol1023745
Volume 12
Issue 23
Start page 5506
End page 5509
Total pages 4
Place of publication Washington, United States
Publisher American Chemical Society
Language eng
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.
Keyword Quantum chemical characterization
DFT Analysis
Cations
Allenamides
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
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