Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 28, Pages 15266-15270Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202103479
Keywords
allylation; cobalt; homogeneous catalysis; photoredox; stereoselectivity
Categories
Funding
- MINECO [CTQ2017-88920-P]
- AGAUR [2017-SGR-232]
- Ministerio de Ciencia e Innovacion (Severo Ochoa Excellence Accreditation 2020-2023) [CEX2019-000925-S]
- European Community [889754]
- ICREA
- Cerca program/Generalitat de Catalunya
- Marie Curie Actions (MSCA) [889754] Funding Source: Marie Curie Actions (MSCA)
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An efficient Co/organophotoredox dual catalysis protocol has been developed for the stereoselective access to a wide variety of syn-configured 1,3-diols with quaternary carbon centers. Mechanistic control experiments suggest that the stereoselectivity is rationalized via a preferred Zimmerman-Traxler transition state. This newly developed process expands the use of base metal catalysis in constructing challenging quaternary carbon stereocenters.
An efficient and attractive Co/organophotoredox dual catalysis protocol has been developed allowing the stereoselective access to a wide variety of syn-configured 1,3-diols featuring quaternary carbon centers. The synthesis of the target molecules is achieved under ambient reaction conditions using modular and accessible reagents, substituted vinyl cyclic carbonates and aldehydes, and in short reaction times. Mechanistic control experiments suggest that the stereoselectivity can be rationalized via a preferred Zimmerman-Traxler transition state comprising a Co(allyl) species and an activated aldehyde. This newly developed process thus expands the use of base metal catalysis in the construction of challenging quaternary carbon stereocenters.
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