Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair Pathway
Publication type: Journal Article
Publication date: 2008-06-11
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
18543924
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
In this work, the one-step diastereoselective synthesis of cis-2,5-disubstituted tetrahydrofurans via Lewis acid catalyzed [3 + 2] cycloadditions of donor−acceptor (D−A) cyclopropanes and aldehydes is described. The scope and limitations with respect to both reaction partners are provided. A detailed examination of the mechanism has been performed, including stereochemical analysis and electronic profiling of both reactants. Experimental evidence supports an unusual stereospecific intimate ion pair mechanism wherein the aldehyde functions as a nucleophile and malonate acts as the nucleofuge. The reaction proceeds with inversion at the cyclopropane donor site and allows absolute stereochemical information to be transferred to the products with high fidelity. The mechanism facilitates the stereospecific synthesis of a range of optically active tetrahydrofuran derivatives from enantioenriched D−A cyclopropanes.
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367
Total citations:
367
Citations from 2025:
11
(3%)
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Pohlhaus P. D. et al. Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair Pathway // Journal of the American Chemical Society. 2008. Vol. 130. No. 27. pp. 8642-8650.
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Pohlhaus P. D., Sanders S. D., Parsons A. T., Li W., Johnson J. S. Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair Pathway // Journal of the American Chemical Society. 2008. Vol. 130. No. 27. pp. 8642-8650.
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RIS
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TY - JOUR
DO - 10.1021/ja8015928
UR - https://doi.org/10.1021/ja8015928
TI - Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair Pathway
T2 - Journal of the American Chemical Society
AU - Pohlhaus, Patrick D
AU - Sanders, Shanina D
AU - Parsons, Andrew T
AU - Li, Wei
AU - Johnson, Jeffrey S.
PY - 2008
DA - 2008/06/11
PB - American Chemical Society (ACS)
SP - 8642-8650
IS - 27
VL - 130
PMID - 18543924
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2008_Pohlhaus,
author = {Patrick D Pohlhaus and Shanina D Sanders and Andrew T Parsons and Wei Li and Jeffrey S. Johnson},
title = {Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair Pathway},
journal = {Journal of the American Chemical Society},
year = {2008},
volume = {130},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ja8015928},
number = {27},
pages = {8642--8650},
doi = {10.1021/ja8015928}
}
Cite this
MLA
Copy
Pohlhaus, Patrick D., et al. “Scope and Mechanism for Lewis Acid-Catalyzed Cycloadditions of Aldehydes and Donor−Acceptor Cyclopropanes: Evidence for a Stereospecific Intimate Ion Pair Pathway.” Journal of the American Chemical Society, vol. 130, no. 27, Jun. 2008, pp. 8642-8650. https://doi.org/10.1021/ja8015928.