Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8628-8633Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03346
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Funding
- Marie Sklodowska-Curie actions [GA 786683]
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
- AstraZeneca
- Diamond Light Source
- Defence Science and Technology Laboratory
- Evotec
- GlaxoSmithKline
- Janssen
- Novartis
- Pfizer
- Syngenta
- Takeda
- UCB
- Vertex
- EPSRC [EP/S013172/1]
- EPSRC [EP/S013172/1] Funding Source: UKRI
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Bicyclo[1.1.1]pentanes (BCPs) are synthesized efficiently using organophotoredox and hydrogen atom transfer catalysis, allowing for the preparation of alpha-quaternary BCPs. The products can be further transformed into a variety of useful derivatives, including enantioenriched BCPs.
Bicyclo[1.1.1]pentanes (BCPs) are important in drug design as sp(3)-rich bioisosteres of arenes and tert-butyl groups; however, the preparation of BCPs with adjacent quaternary carbons is barely known. We report a facile synthesis of alpha-quaternary BCPs using organophotoredox and hydrogen atom transfer catalysis in which alpha-keto radicals, generated through oxidation of beta-ketocarbonyls, undergo efficient addition to [1.1.1]propellane. The BCP products can be transformed into a variety of useful derivatives, including enantioenriched BCPs featuring alpha-quaternary stereocenters.
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