期刊
CHEMICAL RECORD
卷 16, 期 4, 页码 1787-1806出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.201600030
关键词
aminocatalysis; cascade catalysis; enantioselectivity; organocatalysis; vinylogous reactivity
资金
- Institute of Chemical Research of Catalonia (ICIQ) Foundation
- European Research Council (ERC) [278541 - ORGA-NAUT]
- Marie Curie COFUND action [2014-1-ICIQ-IPMP]
- Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- ICREA Funding Source: Custom
Cascade reactions are powerful tools for rapidly assembling complex molecular architectures from readily available starting materials in a single synthetic operation. Their marriage with asymmetric organocatalysis has led to the development of novel techniques, which are now recognized as reliable strategies for the one-pot enantioselective synthesis of stereochemically dense molecules. In recent years, even more complex synthetic challenges have been addressed by applying the principle of vinylogy to the realm of organocascade catalysis. The key to the success of vinylogous organocascade reactions is the unique ability of the chiral organocatalyst to transfer reactivity to a distal position without losing control on the stereo-determining events. This approach has greatly expanded the synthetic horizons of the field by providing the possibility of forging multiple stereocenters in remote positions from the catalyst's point of action with high selectivity, while simultaneously constructing multiple new bonds. This article critically describes the developments achieved in the field of enantioselective vinylogous organocascade reactions, charting the ideas, the conceptual advances, and the milestone reactions that have been essential for reaching highly practical levels of synthetic efficiency.
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