期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 14, 页码 4674-4685出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo100695z
关键词
-
资金
- National Science Foundation
- National Institutes of Health [CA17918]
Two complementary chiral catalysts, the phosphine 8d and the DMAP-derived ent-23b, are used simultaneously to selectively activate a mixture of two different achiral anhydrides as acyl donors under homogeneous conditions. The resulting activated intermediates 25 and 26 react with the racemic benzylic alcohol 5 to form enantioenriched esters (R)-24 and (S)-17 by fully catalytic parallel kinetic resolution (PKR). The aroyl ester (R)-24 is obtained with near-ideal enantioselectivity for the PKR process, but (S)-17 is contaminated by ca. 8% of the minor enantiomer (R)-17 resulting from a second pathway via formation of mixed anhydride 27 and its activation by 8d.
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