Erratum: Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers (J. Am. Chem. Soc. (2011) 133:51 (20708?20711) DOI: 10.1021/ja209270e)

Article abstract of DOI:10.1021/jacs.1c03211

Pages 20709 and 20710. In the published version of the paper, the trans:cis ratios of 2w and 2x were reversed. The revised results were confirmed by NOE experiments and comparison of the optical rotation data with reported values after transformation. The

Full text of DOI:10.1021/jacs.1c03211

pubs.acs.org/JACS
Addition/Correction
Correction to “Oxazaborolidinium Ion-Catalyzed Cyclopropanation
of α‑Substituted Acroleins: Enantioselective Synthesis of
Cyclopropanes Bearing Two Chiral Quaternary Centers”
Lizhu Gao, Geum-Sook Hwang,* and Do Hyun Ryu*
J. Am. Chem. Soc. 2011, 133 (51), 20708−20711. DOI: 10.1021/ja209270e
Cite This: J. Am. Chem. Soc. 2021, 143, 6021−6022
Read Online
sı
*
Metrics & More
Article Recommendations
Supporting Information
ACCESS
Pages 20709 and 20710. In the published version of the paper,
the trans:cis ratios of 2w and 2x were reversed. The revised
results were confirmed by NOE experiments and comparison of
the optical rotation data with reported values after trans-
formation. The corrected Table 3 is presented below. This
correction does not affect the conclusion of the paper.
In the Supporting Information file presenting experimental
details, the absolute configurations of 2w and 2x were
incorrectly drawn as (1R,2R) (pages S26−S28). The corrected
file, available here, depicts the (1S,2R) configurations.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge at
https://pubs.acs.org/doi/10.1021/jacs.1c03211.
■
sı
Experimental procedures and analytical data (corrected)
(PDF)
Published: April 7, 2021
https://doi.org/10.1021/jacs.1c03211
J. Am. Chem. Soc. 2021, 143, 6021−6022
© 2021 American Chemical Society
6021

Journal of the American Chemical Society
pubs.acs.org/JACS
Addition/Correction
Table 3. Asymmetric Cyclopropanation of Various Diazoacetates and α-Substituted Acroleins Catalyzed by 1b
a
b
c
entry
R1, R2
2
T (°C), t (h)
trans:cis
yield (%)
ee (%)
1
2
3
4
5
6
7
8
Me, 4-BrPh
Br, 4-BrPh
Cl, 4-BrPh
Me, 2-MePh
Br, 2-MePh
Cl, 2-MePh
Cl, 3-MePh
Cl, 4-MePh
Cl, 3-MeOPh
Cl, 4-MeOPh
Br, 4-NO2Ph
Cl, H
2l
−45, 1
−25, 5
−25, 5
−45, 6
−45, 0.5
−45, 0.5
−45, 0.5
−78, 6
−45, 1
−78, 2
0, 18
80:20
95:5
96:4
72
93
93
83
88
89
95
92
90
94
93
95
95
95
95
92
95
95
2m
2n
2o
2p
2q
2r
2s
2t
2u
2v
2w
2x
92:8
90:10
90:10
92:8
d
87
88
d
93:7
85
87
9
90:10
55:45
92:8
9:91
9:91
e
10
11
12
13
51
d
71
f
−78, 2
−78, 1
85
f
Br, H
80
a
b
c
Determined by 1H NMR analysis of the crude reaction mixture. Isolated yield. The ee of the product was determined by chiral HPLC or GC.
d
e
Yield of the trans isomer was calculated by 1H NMR analysis of the isolated mixture of isomers. The cis isomer was obtained in 43% yield with
f
1
94% ee. The cis isomer was obtained as the major product, and the yield of the cis isomer was calculated by H NMR analysis of the isolated
mixture of isomers.
6022
https://doi.org/10.1021/jacs.1c03211
J. Am. Chem. Soc. 2021, 143, 6021−6022