Journal
ORGANIC LETTERS
Volume 14, Issue 21, Pages 5590-5593Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol302711w
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Funding
- ICIQ Foundation
- MICINN [CTQ2010-15513]
- European Research Council [278541-ORGA-NAUT]
- ICREA Funding Source: Custom
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The direct vinylogous aldol reaction of alpha-substituted alpha,beta-unsaturated aldehydes with isatins is described. The chemistry provides easy access to valuable 3-substituted 3-hydroxyoxindole derivatives with high stereocontrol and perfect gamma-site selectivity. Preliminary mechanistic studies suggest that, depending on the nature of the a-branched enal substituents, two divergent reaction mechanisms can be operating, leading to different products and stereochemical outcomes.
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