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On the Origin of Altered Diastereomeric Ratios for Anionic versus Neutral Reaction Conditions in the Oxy-Cope/Ene Reaction: An Interplay of Experiment and Computational Modeling

Autor: Tom K. Woo, James Hooper, Effiette L. O. Sauer, Steve Arns, Louis Barriault

Publikováno v: Chemistry - A European Journal. 16:14124-14130

We report herein a detailed investigation into the reaction mechanism for a sequential oxy-Cope/ene reaction under anionic conditions. With DFT calculations and ab initio molecular dynamics simulations, the observed diastereoselectivity is shown to b

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4255cbcc27a238a990022152c16ac39d
https://doi.org/10.1002/chem.201001302

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Iridium and Ruthenium Complexes with Chelating N-Heterocyclic Carbenes: Efficient Catalysts for Transfer Hydrogenation, β-Alkylation of Alcohols, and N-Alkylation of Amines

Autor: Effiette L. O. Sauer, Nathan D. Schley, Robert H. Crabtree, Christopher D. Incarvito, Chase Butler, Dinakar Gnanamgari

Publikováno v: Organometallics. 28:321-325

Air-stable Ir and Ru complexes of a chelating pyrimidine-functionalized N-heterocyclic carbene were synthesized. The complexes were characterized by NMR spectroscopy and single-crystal X-ray diffraction and were found to be catalytically active for t

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::4d8e0d71fdbbac05483e29821980fafa
https://doi.org/10.1021/om800821q

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Synthesis and Reactivity of N-Hydroxy-2-Amino-3-Arylindoles

Autor: Laird A. Trimble, Gabriel St-Pierre, Daniel Beaudoin, Michel Belley, Effiette L. O. Sauer, Petar Duspara

Publikováno v: Synlett. 2007:2991-2994

Catalytic hydrogenation of 2-nitrophenylacetonitriles bearing an aromatic substituent a to the nitrile group, using Pd/C and (Ph 3 P) 4 Pd, affords unstable N-hydroxy-2-amino-3-arylindoles which, after autoxidation, yields 2-amino-3-aryl-3H-indol-3-o

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::a22c0c72592181e90d5efea524d09742
https://doi.org/10.1055/s-2007-990969

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Origin of Diastereoselectivity in the Tandem Oxy-Cope/Claisen/Ene Reaction: Experimental and Theoretical Studies of the Ring Inversion Mechanism

Autor: Effiette L. O. Sauer, James Hooper, Tom K. Woo, Louis Barriault

Publikováno v: Journal of the American Chemical Society. 129:2112-2119

We report herein a detailed investigation into the reaction mechanism of the oxy-Cope/Claisen/ene reaction. A series of chiral substrates was prepared, subjected to the tandem sequence, and the enantiomeric excess of the final products was evaluated.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d48aac4eeda0fc4748e4638d96696a41
https://doi.org/10.1021/ja066830f

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Studies toward the Total Synthesis of Wiedemannic Acid

Autor: Louis Barriault, Effiette L. O. Sauer

Publikováno v: Organic Letters. 6:3329-3332

[reaction: see text] We report a novel and efficient diastereoselective synthesis of wiedemannic acid analogue 30 in 16 steps from 7 using a tandem oxy-Cope/Claisen/ene reaction as the key step. Comparison of NMR data between wiedemannic acid (1) and

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a195cad84b27bdaba6fc1498d8c892d6
https://doi.org/10.1021/ol0487635

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Reaction of the tamoxifen cation and the bis-(4-methoxyphenyl)methyl cation in aqueous solutions containing 2'-deoxyguanosine

Autor: Effiette L. O. Sauer, Sinisa Vukovic, Cristina Sanchez, Robert A. McClelland

Publikováno v: Canadian Journal of Chemistry. 80:269-280

The competition between 2'-deoxyguanosine (dG) and water has been quantitatively evaluated for the allylic carbocation derived from tamoxifen and for the stabilized diarylmethyl cation (bis-(4-methoxyphenyl)methyl). Both systems were examined by the

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::518e59ae92637512651cb05b9779b251
https://doi.org/10.1139/v02-011

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Enantioselective Allylation of β,γ-Unsaturated Aldehydes Generated via Lewis Acid Induced Rearrangement of 2-Vinyloxiranes

Autor: Effiette L. O. Sauer, Matthew L. Maddess, Mark Lautens, Stephane G. Ouellet

Publikováno v: Organic Letters. 4:83-86

[reaction: see text] 2-Vinyloxiranes have been found to be excellent surrogates to beta,gamma-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)(3), are effective

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::cf58d4b497bb6f6450628e6241b1f76d
https://doi.org/10.1021/ol016946a

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Manganese Catalysts for C–H activation: An Experimental/Theoretical Study Identifies the Stereoelectronic Factor that Controls the Switch between Hydroxylation and Desaturation Pathways

Autor: David Balcells, Christophe Raynaud, Odile Eisenstein, Effiette L. O. Sauer, Robert H. Crabtree, Gary W. Brudvig, Jonathan F. Hull

Publikováno v: Journal of the American Chemical Society
Journal of the American Chemical Society, American Chemical Society, 2010, 132 (22), pp.7605-7616. ⟨10.1021/ja908744w⟩

International audience; We describe competitive C−H bond activation chemistry of two types, desaturation and hydroxylation, using synthetic manganese catalysts with several substrates. 9,10-Dihydrophenanthrene (DHP) gives the highest desaturation a

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a76a1a089b23c4e6bf8e0ce4261dbef1
https://europepmc.org/articles/PMC2903729/

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