Organic Letters, volume 14, issue 24, pages 6302-6305
Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes
Publication type: Journal Article
Publication date: 2012-12-11
Journal:
Organic Letters
Q1
Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
PubMed ID:
23231774
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The cyclometalated π-allyliridium 3,4-dinitro-C,O-benzoate complex modified by (R)- or (S)-Cl,MeO-BIPHEP promotes the transfer hydrogenative coupling of allyl acetate to β-stereogenic alcohols with good to excellent levels of catalyst-directed diastereoselectivity to furnish homoallylic alcohols. Remote electronic effects of the C,O-benzoate of the catalyst play a critical role in suppressing epimerization of the transient α-stereogenic aldehyde.
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Schmitt D., Dechert Schmitt A. M. R., Krische M. J. Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes // Organic Letters. 2012. Vol. 14. No. 24. pp. 6302-6305.
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Schmitt D., Dechert Schmitt A. M. R., Krische M. J. Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes // Organic Letters. 2012. Vol. 14. No. 24. pp. 6302-6305.
Cite this
RIS
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TY - JOUR
DO - 10.1021/ol3030692
UR - https://doi.org/10.1021/ol3030692
TI - Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes
T2 - Organic Letters
AU - Schmitt, Daniel
AU - Dechert Schmitt, Anne Marie R
AU - Krische, Michael J
PY - 2012
DA - 2012/12/11
PB - American Chemical Society (ACS)
SP - 6302-6305
IS - 24
VL - 14
PMID - 23231774
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2012_Schmitt,
author = {Daniel Schmitt and Anne Marie R Dechert Schmitt and Michael J Krische},
title = {Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes},
journal = {Organic Letters},
year = {2012},
volume = {14},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ol3030692},
number = {24},
pages = {6302--6305},
doi = {10.1021/ol3030692}
}
Cite this
MLA
Copy
Schmitt, Daniel, et al. “Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes.” Organic Letters, vol. 14, no. 24, Dec. 2012, pp. 6302-6305. https://doi.org/10.1021/ol3030692.