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M. Bhanushali, C.-G. Zhao / Tetrahedron Letters 53 (2012) 359–362
(Fig. 2) in the presence of racemic 1,10-binaphthyl-2,20-diyl hydro-
gen phosphate (19, Fig. 2) as a cocatalyst,12 and the corresponding
aldol product 4k was obtained in a 94% yield with a diastereoselec-
tivity of 82:18 and an ee value of 79% for the major diastereomer
(entry 11). Similar results were obtained for the methyl ester 2g,
where the product 4l was obtained in a dr of 75:25 with 78% ee
for the major diastereomer (entry 12).
In conclusion, we have developed the first enantioselective syn-
thesis of 3-alkyl-3-hydroxy-1H-pyrrol-2(3H)-one derivatives (up
to 94% ee) using a cross aldol reaction between 1-benzyl 4,5
-dioxo-2-aryl-4,5-dihydro-1H-pyrrole-3-carboxylates and ketones.
Chem. 2010, 75, 1101–1106; (e) Dodda, R.; Zhao, C.-G. Synlett 2007, 1605–1609;
(f) Guo, Q.; Bhanushali, M.; Zhao, C.-G. Angew. Chem., Int. Ed. 2010, 49, 9460–
9464; (g) Perera, S.; Naganaboina, V.; Wang, L.; Zhang, B.; Guo, Q.; Rout, L.;
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logues were found to be the best catalysts. The reaction was also
found to be very sensitive toward steric hindrance and, therefore,
for cyclohexanone, the best results were achieved with 9-deoxy-
9-epi-aminoquinine (18) as the catalyst in the presence racemic
1,10-binaphthyl-2,20-diyl hydrogen phosphate (19) as the
cocatalyst.
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Acknowledgments
The generous financial support of this project from the NIH/
NIGMS (Grant No. SC1GM082718) and the Welch Foundation
(Grant No. AX-1593) is gratefully acknowledged.
Supplementary data
Supplementary data associated with this article can be found, in
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11. For details, please see Table S-1 in the Supplementary data.
12. When (R)-1,10-binaphthyl-2,20-diyl hydrogen phosphate [(R)-19] was used as
the cocatalyst, no difference in reactivity and enantioselectivity was observed
as compared with that conducted with racemic 19.