Erratum: Diastereoselective Ni-catalyzed negishi cross-coupling approach to saturated, fully oxygenated C-Alkyl and C-Aryl glycosides

Full text of DOI:10.1021/ja300641c

Addition/Correction
pubs.acs.org/JACS
Correction to Diastereoselective Ni-Catalyzed Negishi
Cross-Coupling Approach to Saturated, Fully Oxygenated
C-Alkyl and C-Aryl Glycosides
Hegui Gong and Michel R. Gagne*
́
J. Am. Chem. Soc., 2008, 130, 12177−12183. DOI: 10.1021/ja8041564
Page 12181. The original equation for Table 6 incorrectly had a
mannose being converted to a glucose. The corrected graphic
and original data is given below. We thank an observant reader
for bringing this to our attention.
Table 6. Reaction Optimization for PhZnI·LiCl and Aceto-α-
Br-D-mannose
a
entry
conditions
product (α:β)
glucal
1
2
3
4
5
6
7
NiCl2·glyme, PyBox, DMI
Ni(COD)2, PyBox, DMA
Ni(COD)2, Terpy, DMA
40% (α)
30%
15%
trace
15%
7%
∼30% (α)
56% (6.6:1)
65% (1.6:1)
80% (20:1)
79% (10:1)
76% (2.9:1)
t
Ni(COD)2, Bu-Terpy, DMA
Ni(COD)2, PyBox, DMF
Ni(COD)2, Terpy, DMF
10%
10%
t
Ni(COD)2, Bu-Terpy, DMF
a
Reaction conditions: mannosyl bromide (0.24 mmol, 0.19 M in
DMF), Ni(COD)2 (0.024 mmol), ligand (0.036 mmol), and
PhZnI·LiCl (∼0.5 M in DMF) at rt for 12 h.
Published: March 9, 2012
© 2012 American Chemical Society
5423
dx.doi.org/10.1021/ja300641c | J. Am. Chem. Soc. 2012, 134, 5423−5423