Erratum to: Enantioselective Intramolecular Friedel-Crafts-Type α-Arylation of Aldehydes (Journal of the American Chemical Society (2009) 131 (2086-2087))

Full text of DOI:10.1021/ja902682t

Residue-Specific pKa Determination of Lysine and
Arginine Side Chains by Indirect 15N and 13C NMR
Spectroscopy: Application to apo Calmodulin [J. Am.
Chem. Soc. 2007, 129, 15805–15813]. Ingemar Andre´,
Sara Linse, and Frans A. A. Mulder*
Enantioselective Intramolecular Friedel-Crafts-Type
r-Arylation of Aldehydes [J. Am. Chem. Soc. 2009,
131, 2086–2087]. K. C. Nicolaou,* Ru¨diger Reingruber,
David Sarlah, and Stefan Bra¨se
Page 2086. The intermediate in eq 1 should be a cation radical
as follows:
Page 15807. A typographical mistake was found in eq 1. The
correct form of the Henderson-Hasselbalch equation for
deprotonation should read
(δHA + δA- 10(pH-pK )
)
a
δobs
)
(1)
(1 + 10(pH-pK )
)
a
The structures 1b and A in Table 1 should be as follows:
-
where δobs is the observed chemical shift and δHA and δA are
the chemical shifts of the protonated and unprotonated forms,
respectively.
Importantly, all data were analyzed with this correct form of
eq 1, and in no way does this correction change the results or
conclusions presented in the original paper. We thank Mr. Jelle
Slager for bringing this mistake to our attention.
The intramolecular attack from the aromatic nucleus occurs
from the Re face of the enamine when using (2R,5R)-A.
Page 2087. The structures of the products in Table 2, entries
3 and 10, should be as follows:
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Correspondingly, Scheme 1 should be corrected as follows:
Ligand Controlled Highly Regio- and Enantioselec-
tive Synthesis of r-Acyloxyketones by Palladium-
Catalyzed Allylic Alkylation of 1,2-Enediol Carbo-
nates [J. Am. Chem. Soc. 2008, 130, 11852–11853].
Barry M. Trost,* Jiayi Xu, and Thomas Schmidt
Page 11853. In Table 2, entries 11 and 12, the stereochemical
assignments of the cyclohexenyl ring of compound 20 and the
cycloheptenyl ring of compound 22 should be S, not R. This
assignment is based on the empirical model we proposed (Trost,
B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545), which
has been supported by extensive experimental data.
We deeply regret these oversights and errors. A corrected
Supporting Information file that reflects these changes is
available. These corrections have no implications on the main
discoveries and conclusions described in the paper.
Supporting Information Available: Experimental proce-
dures and compound characterization (corrected). This material
is available free of charge via the Internet at http://pubs.acs.org.
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6640 J. AM. CHEM. SOC. 2009, 131, 6640–6641
10.1021/ja902385j CCC: $40.75  2009 American Chemical Society

A D D I T I O N S & C O R R E C T I O N S
Valence Anions of 9-Methylguanine-1-Methylcytosine
Complexes. Computational and Photoelectron Spec-
troscopy Studies [J. Am. Chem. Soc. 2009, 131,
Jacobsen’s Catalyst for Hydrolytic Kinetic Resolu-
tion: Structure Elucidation of Paramagnetic Co(III)
Salen Complexes in Solution via Combined NMR and
Quantum Chemical Studies [J. Am. Chem. Soc. 2009,
131, 4172–4173]. Sebastian Kemper, Peter Hroba´rik,
Martin Kaupp,* and Nils E. Schlo¨rer*
2663–2669].
Anna
Szyperska,
Janusz
Rak,*
Jerzy Leszczynski,* Xiang Li, Yeon Jae Ko, Haopeng Wang,
and Kit H. Bowen*
Page 2668. In the last paragraph of section 3.2.2, the
activation barrier for the proton transfer process from the N1
atom of methylguanine to the N3 atom of methylcytosine should
be corrected as written below:
Page 4173. Footnote a of Scheme 2 should read “S-epoxide”
instead of “R-epoxide”.
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The kinetic barrier that separates a1MGMC and
a1MGMC_SPT2 structures is 2.78 and 2.39 kcal/mol in terms
of energy and free energy, respectively.
The conclusion remains the same.
Page 2663-2664. An important reference was inadvertently
omitted from the Introduction. Schaefer and co-workers1 used
the B3LYP/DZP++ theoretical approach to study the 2′-
deoxyguanosine-2′-deoxycytidine (dG:dC) nucleoside pair. Their
research revealed that electron attachment to the dC moiety in
the dG:dC pair is able to trigger proton transfer from N1(dG)
to N3(dC), forming the more stable anionic complex d(G-H)-:
d(C+H)•, and the energy barrier for this reaction is 2.4 kcal/
mol, which is in good agreement with data presented in our
article.
Literature Cited
(1) Gu, J.; Xie, Y.; Schaefer, H. F., III J. Chem. Phys. 2007, 127,
155107/1–155107/6.
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