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. 2016 Jun 1;5(3):267. doi: 10.1002/open.201600044

Corrigendum: Sterically Demanding Unsymmetrical Diaryl‐λ3‐iodanes for Electrophilic Pentafluorophenylation and an Approach to α‐Pentafluorophenyl Carbonyl Compounds with an All‐Carbon Stereocenter

Kohei Matsuzaki, Kenta Okuyama, Etsuko Tokunaga, Motoo Shiro, Norio Shibata
PMCID: PMC4984412  PMID: 27551663

The authors found that there is an error in the absolute stereochemistry of 5 e in Figure 1. The authors showed (R)‐5 e, but is should be (S)‐5 e. The correct Figure 1 is shown, and the corresponding sentence (page 235, line 8, second column), should read:

Figure 1.

Figure 1

X‐ray crystallographic structure of (S)‐5 e (CCDC 1009021).

“The absolute configuration of 5 e was determined as S by X‐ray crystallography (Figure 1), and the stereochemistry of 5 a–d, 5 f–i was tentatively assigned by analogy.”

Based on this correction, the stereochemistry of compounds 5 in Scheme 1, Table 3, and Scheme 1, 1, 2 should be corrected as follows (corrections are shown in red):

Scheme 1.

Scheme 1

Electrophilic pentafluorophenylation by 1 and transformations to chiral α‐pentafluorophenyl ketones having an all‐carbon stereocenter.

Table 1.

Creation of an all‐carbon stereogenic center with C6F5: asymmetric alkylation of α‐pentafluorophenyl ketones 4 with R−Br under organocatalysis.[a]

graphic file with name OPEN-5-267-g004.jpg
Entry 4, n R Time [h] 5 Yield[b] [%] ee [c] [%]
1[d] 4 a, n=1 allyl 96 5 a 95 87 (−)
2 4 a, n=1 benzyl 24 5 b 95 96 (+)
3 4 a, n=1 CH2p‐Tol 48 5 c 91 96 (−)
4[e] 4 a, n=1 CH2p‐MeOPh 72 5 d 84 95 (−)
5 4 a, n=1 CH2p‐BrPh 48 5 e 87 98 (−)
6 4 a, n=1 CH2‐1‐Naphthyl 96 5 f 83 92 (+)
7 4 a, n=1 CH2‐2‐Naphthyl 24 5 g 89 94 (−)
8 4 b, n=2 benzyl 48 5 h 93 96 (−)

[a] Reagents and conditions: a) R−Br (2.0 equiv), 7 (10 mol %), aq KOH (50 wt %), toluene, −40 °C, time. All reactions were carried out using 7 a as a catalyst unless noted otherwise. [b] Isolated yield. [c] Determined by HPLC analysis. [d] Catalyst 7 b was used instead of 7 a. [e] R−Br (1.2 equiv) was employed.

Scheme 2.

Scheme 2

Creation of an all‐carbon stereogenic center with C6F5: palladium‐catalyzedasymmetric decarboxylative allylation of 3 d and 3 o using the Trost ligand.

This correction does not influence any of the data presented in the article, nor its interpretation. The authors apologize for these mistakes.


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