Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 10, Pages 3313-3317Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509472
Keywords
asymmetric catalysis; Diels-Alder reactions; organocatalysis; photochemistry; synthetic methods
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Funding
- ICIQ Foundation
- MINECO [CTQ2013-45938-P, SEV-2013-0319]
- CELLEX Foundation
- AGAUR [2014 SGR 1059]
- European Research Council [ERC 278541-ORGA-NAUT]
- Marie Curie COFUND action [2014-1-ICIQ-IPMP]
- CONACyT (Consejo Nacional de Ciencia y Tecnologia, Mexico) [237346]
- ICREA Funding Source: Custom
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The photoenolization/Diels-Alder strategy offers straightforward access to synthetically valuable benzannulated carbocyclic products. This historical light-triggered process has never before succumbed to efforts to develop an enantioselective catalytic approach. Herein, we demonstrate how asymmetric organocatalysis provides simple yet effective catalytic tools to intercept photochemically generated hydroxy-o-quinodimethanes with high stereoselectivity. We used a chiral organic catalyst, derived from natural cinchona alkaloids, to activate maleimides toward highly stereoselective Diels-Alder reactions. An unconventional mechanism of stereocontrol is operative, wherein the organocatalyst is actively involved in both the photochemical pathway, by leveraging the formation of the reactive photoenol, and the stereoselectivity-defining event.
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