Correction to a facile access to enantioenriched isoindolines via one-pot sequential cu(I)-catalyzed asymmetric 1,3-dipolar cycloaddition/oxidation (Organic Letters (2012) 14, 24 (6230-6233) 10.1021/ol302987h)

Full text of DOI:10.1021/ol5025458

Addition/Correction
pubs.acs.org/OrgLett
Correction to A Facile Access to Enantioenriched Isoindolines via
One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar
Cycloaddition/Oxidation
Zhao-Lin He, Tang-Lin Liu, Haiyan Tao, and Chun-Jiang Wang*
Org. Lett. 2012, 14 (24), 6230−6233. DOI: 10.1021/ol302987h
S
* Supporting Information
n incorrect X-ray structure and CIF file caused misinter-
pretation of the structures of 5a−r and 7. See below for
The Abstract/TOC graphic, Schemes 1−3, Tables 1 and 2,
A
and Figure 1 should be replaced.
corrections to the paper and the Supporting Information. Com-
plete corrected Supporting Information and a corrected CIF for
5b are included.
We thank Professor Dr. Alex M. Szpilman for his kindly
pointing out the mistakes.
Page 6230: The title should be “A Facile Access to Enantio-
enriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed
Asymmetric 1,3-Dipolar Cycloaddition/Oxidation”.
Page 6230, Abstract text, line 3: “aromatization” should be
replaced by “oxidation”.
Page 6231, right column, lines 1 and 37; page 6232, right column,
lines 3 and 30; page 6233, right column, line 6: “aromatization”
should be replace by “oxidation”.
Page 6321, right column, line 21, “significant” should be
replaced by “partially”; line 23, “efficiently” should be replaced
by “partially”; line 34, “keto-isomer” should be replaced by
“precursor”.
ASSOCIATED CONTENT
■
S
* Supporting Information
Corrected structures are provided for 5a−r and compound 7.
Several compounds have a proton in the spectra between 2.60
and 2.70 ppm that was not reported in the experimental details
section; see the updated 1H NMR reporting for compounds 5a,
5d, 5f, 5g, 5i, and 5o. There are fewer reported 1H NMR peaks
in the experimental details section than in the spectrum for
1
compound(s) 5b and 5n; see the updated H NMR reporting
Scheme 3. Catalyst asymmetric one-pot sequential
1,3-DC/Oxidation of Benzoquinone 6 and imino ester 4a
Scheme 1
Scheme 2
Received: September 9, 2014
Published: September 30, 2014
© 2014 American Chemical Society
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dx.doi.org/10.1021/ol5025458 | Org. Lett. 2014, 16, 5506−5507

Organic Letters
Addition/Correction
Table 2. Substrates Scope of One-Pot and Sequential
Table 1. Optimization of One-Pot and Sequential Catalytic
Asymmetric 1,3-DC/Oxidation of Imino Ester 4a with
Naphthoquinone 2.
Asymmetric 1,3-DC/Oxidation of Imino Ester 4 with
a
a
Napthoquinone 2
b
c
entry
R1
Ph (4a)
R2
5
yield (%)
ee (%)
1
2
3
4
Bn
Bn
Bn
Bn
Bn
Bn
Bn
Bn
Bn
Bn
Bn
Bn
Bn
Me
Et
5a
5b
5c
5d
5e
5f
86
89
87
87
87
93
81
86
81
85
79
76
70
82
90
77
74
86
96
95
94
94
92
95
93
97
96
94
97
94
94
89
94
90
93
93
p-Cl-C6H4 (4b)
o-Cl-C6H4 (4c)
m-Cl-C6H4 (4d)
p-CF3-C6H4 (4e)
p-Me-C6H4 (4f)
o-Me-C6H4 (4g)
m-Me-C6H4 (4h)
p-MeO-C6H4 (4i)
o-MeO-C6H4 (4j)
2-naphthyl (4k)
2-furyl (41)
d
5
6
7
5g
5h
5i
8
9
10
5j
d
11
5k
51
5m
5n
5o
5p
5q
5r
12
13
14
15
Cy (4m)
Ph (4n)
Ph (4o)
d
16
Ph (4p)
Pr
i-Bu
d
17
d
Ph (4q)
18
Ph (4r)
Ph
a
Unless otherwise noted, the reaction was carried out with 0.26 mmol
b
of 4 and 0.20 mmol of 2 in 2 mL of toluene at −20 °C. Isolated yield.
c
d
Ee was determined by HPLC analysis. Carried out at 0 °C.
a
All reactions were carried out with 0.26 mmol of 4a and 0.20 mmol of
b
c
2 in 2 mL of solvent. CuBF4 = Cu(CH3CN)4BF4. Isolated yield. Ee
was determined by HPLC analysis.
for 5b: 7.88 (d, J = 7.5 Hz) should be replaced by 7.88 (d, J =
7.5 Hz, 1H); 5n: 7.44 (d, J = 6.9 Hz, 1H) should be replaced by
1
7.44 (d, J = 6.9 Hz, 2H). There are more reported H NMR
Figure 1. X-ray structure of (1R,3R)-5b.
peaks in the experimental details section than in the spectrum
for compound 5r; see the updated H NMR reporting for 5r:
1
7.40−7.24 (m, 8H) should be replaced by 7.40−7.24 (m, 6H).
This material is available free of charge via the Internet at
http://pubs.acs.org.
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dx.doi.org/10.1021/ol5025458 | Org. Lett. 2014, 16, 5506−5507