期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 355, 期 16, 页码 3124-3130出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300667
关键词
asymmetric catalysis; cascade reactions; organocatalysis; spiro compounds; vinylogous reactivity
资金
- ICIQ Foundation
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2010-15513]
- European Research Council (ERC) [278541 - ORGA-NAUT]
- ICREA Funding Source: Custom
We report a triple vinylogous cascade reaction, yielding valuable spiro-oxindolic cyclohexane derivatives. The three-component domino process proceeds by way of a catalyzed Michael/1,6-addition/vinylogous aldol sequence affording the products with six stereogenic centers and very high control over the stereochemistry. The chemistry is based on a rare example of asymmetric 1,6-addition to linear 2,4-dienals proceeding with complete -site selectivity. Key to the reaction development was a directing group positioned at the -dienal position, which was essential for achieving highly predictable reaction outcomes.
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