Origin of stereoselectivity in the (4 + 3) cycloadditions of chiral alkoxy siloxyallyl cations with furan

Krenske, Elizabeth H., Houk, K. N. and Harmata, Michael (2010) Origin of stereoselectivity in the (4 + 3) cycloadditions of chiral alkoxy siloxyallyl cations with furan. Organic Letters, 12 3: 444-447. doi:10.1021/ol902591k


Author Krenske, Elizabeth H.
Houk, K. N.
Harmata, Michael
Title Origin of stereoselectivity in the (4 + 3) cycloadditions of chiral alkoxy siloxyallyl cations with furan
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
1523-7052
Publication date 2010-02-05
Sub-type Article (original research)
DOI 10.1021/ol902591k
Volume 12
Issue 3
Start page 444
End page 447
Total pages 4
Place of publication Washington, United States
Publisher American Chemical Society
Language eng
Abstract The mechanisms and stereoselectivities of (4 + 3) cycloadditions between chiral alkoxy siloxyallyl cations and furan are examined using density functional theory calculations. These cycloadditions are predicted to take place via stepwise mechanisms. The stereoselectivities of cycloadditions involving siloxyallyl cations derived from chiral α-methyl benzylic alcohols are controlled by two effects: minimization of steric repulsion between the α-Me group and the allyl group and attractive CH−π interactions between the furan and the aryl group.
Keyword Allyl Cations
Model
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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