Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 9, Pages 4555-4560Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202013020
Keywords
enantioselectivity; hydrogen-atom transfer; photocatalysis; pyrrolines; radical-radical coupling
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Funding
- European Research Council (ERC-CoG) [647550, 861930]
- Spanish Government [RTI2018-095038-B-I00]
- Comunidad de Madrid
- European Structural Funds [S2018/NMT-4367]
- European Research Council (ERC) [861930] Funding Source: European Research Council (ERC)
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This study introduces a light-driven, atom-economical process for synthesizing enantiomerically enriched substituted chiral 1-pyrroline derivatives through distal functionalization of acyl heterocycles and the use of tailor-made ketimines as partners. Water is the sole by-product of the reaction, and stereoselectivity is controlled by coordination to a chiral-at-rhodium catalyst.
Herein, a light-driven, atom-economical process that provides access to enantiomerically enriched substituted chiral 1-pyrroline derivatives is introduced. The strategy involves the distal functionalization of acyl heterocycles through a hydrogen-atom transfer (HAT) process and the use of tailor-made ketimines as reliable electrophilic partners. This transformation is translated into an enantiomerically controlled radical/polar cascade reaction in which water is produced as the sole by-product and stereoselectivity is dictated by coordination to a chiral-at-rhodium catalyst.
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