Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 26, Pages 9729-9736Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c04180
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Funding
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine for a studentship [EP/L015838/1]
- AstraZeneca
- Diamond Light Source
- Defence Science and Technology Laboratory
- Evotec
- GlaxoSmithKline
- Jannsen
- Novartis
- Pfizer
- Syngenta
- Takeda
- UCB
- Vertex
- Marie SklodowskaCurie actions [786683]
- EPSRC [EP/S013172/1]
- EPSRC [EP/S013172/1] Funding Source: UKRI
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A facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy is reported, allowing for straightforward access to an array of valuable aniline-like isosteres.
Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp(3)-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of alpha-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C-I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodoBCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.
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