Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 16, Pages 2953-2959Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100499
Keywords
acid derivatives; aldol reaction; asymmetric catalysis; Cinchona alkaloids; hydrogen bonding
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Funding
- Bologna University
- MIUR
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The first enantioselective direct aldol addition of N-Boc-oxindoles to polymeric ethyl glyoxylate is presented. The reaction is performed by using as low as 0.1 mol parts per thousand (DHQ)(2)PHAL and gives access to a-hydroxycarboxylate derivatives bearing adjacent secondary alcohol and quaternary stereocenters with high levels of diastereo- and enantiocontrol. The use of ethyl glyoxylate in its polymeric form represents an important advantage for synthetic applications and allows us to directly install a C-2 unit ready to be converted in useful building blocks. A further one-pot protection/deprotection sequence catalyzed by Zn(ClO4)(2)center dot 6H(2)O preserved the a-hydroxycarboxylates from racemization by means of a parasitic alcohol-catalyzed retroaldol reaction.
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