H.-M. Shen, H.-B. Ji / Tetrahedron Letters 53 (2012) 3541–3545
3545
Table 3 (continued)
Entry
Aldehyde
Ketone
Yielda (%)
67
syn/antia
eea (%)
87/52
Configuration
CHO
CHO
O
21
22
70/30
R/S
O
Trace
N.D.
N.D.
—
CHO
CHO
O
23
24
Trace
47
N.D.
N.D.
—
CH3CCH2CH3
O
60/40
73/38
R/S
CHO
O
25
N.D.
—
—
—
Condition: CD-1 0.04 mmol, aldehyde 0.20 mmol, acetone 0.2 mL + 0.1 mL, solvent(pH 4.5, 0.5 mol/L CH3COONa–HCl) 1 mL, 25 °C, 96.0 h; N.D. (Yield, ee): The yield or ee of
the product was not determined.
a
Determined by HPLC analysis with a Chiralcel AS-H column. The absolute configurations of the aldol products were determined by comparison of the eluting sequence of
the enantiomers with literature.6d
Christensen, B.; Bols, M. Eur. J. Org. Chem. 2005, 2734; (d) Bjerre, J.; Rousseau,
C.; Marinescu, L.; Bols, M. Appl. Microbiol. Biotechnol. 2008, 81, 1.
H2
N
OH
O
O
OH
3. (a) Bjerre, J.; Fenger, T.-H.; Marinescu, L.-G.; Bols, M. Eur. J. Org. Chem. 2007,
704; (b) Marinescu, L.-G.; Doyagueez, E.-G.; Petrillo, M.; Fernandez-Mayoralas,
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Chen, S.; Wu, G.-F.; Chen, H.-Y.; Mao, Z.-W.; Ji, L.-N. Inorg. Chem. Commun. 2011,
14, 184.
N
O2N
NO2
(S)-
(R)-
4. (a) Dong, Z.-Y.; Liu, J.-Q.; Mao, S.-Z.; Huang, X.; Yang, B.; Ren, X.-J.; Luo, G.-M.;
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Int. Ed. 2000, 39, 1267; (b) French, R.-R.; Holzer, P.; Leuenberger, M.; Nold, M.-
C.; Woggon, W.-D. J. Inorg. Biochem. 2002, 88, 295; (c) Breslow, R.; Yan, J.-M.;
Belvedere, S. Tetrahedron Lett. 2002, 43, 363; (d) Yang, J.; Gabriele, B.;
Belvedere, S.; Huang, Y.; Breslow, R. J. Org. Chem. 2002, 67, 5057.
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H
O
H
O
NO2
major
NO2
minor
Figure 4. Schematic origin of enantioselectivity induced by CD-1.
Acknowledgements
The authors thank the National Natural Science Foundation of
China (Nos. 21176268 and 21036009), higher-level talent project
for the Guangdong Provincial Universities and the Fundamental
Research Funds for the Central Universities for providing financial
support to this project.
Supplementary data
Supplementary data associated with this article can be found, in
9. Chen, J.-R.; An, X.-L.; Zhu, X.-Y.; Wang, X.-F.; Xiao, W.-J. J. Org. Chem. 2008, 73,
6006.
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17, 556; (b) Liu, K.; Haeussinger, D.; Woggon, W.-D. Synlett 2007, 2298.
11. (a) Li, D.-B.; Ng, S.-C.; Novak, I. Tetrahedron Lett. 1871, 2002, 43; (b) Park, J.-W.;
Lee, S.-Y.; Song, H.-J.; Park, K.-K. J. Org. Chem. 2005, 70, 9505.
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