期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 50, 页码 21246-21251出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c11244
关键词
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资金
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine - AstraZeneca [EP/L015838/1]
- Diamond Light Source
- Defence Science and Technology Laboratory
- Evotec
- GlaxoSmithKline
- Jannsen
- Novartis
- Pfizer
- Syngenta
- Takeda
- UCB
- Vertex
- EPSRC [EP/S013172/1]
- EPSRC [EP/S013172/1] Funding Source: UKRI
This study presents the synthesis of tri- and tetrasubstituted BCBs through directed metalation of readily accessed BCB amides, providing a late stage approach for generating a wide variety of bridge-substituted BCBs that can be easily converted into other useful small ring building blocks. Access to a monodeuterated BCB also offers unprecedented insight into the mechanism of dihalocarbene insertion into BCBs to afford bicyclo[1.1.1]pentanes (BCPs).
Bicyclo[1.1.0]butanes (BCBs) are valuable substrates in the strain release synthesis of polysubstituted four-membered ring systems, with applications including bioconjugation agents. The introduction of substituents onto the BCB bridges is challenging due to limitations in current methods for the preparation of this bicyclic scaffold, typically necessitating linear syntheses with limited functional group tolerance and/or substituent scope. Here, we report the synthesis of tri- and tetrasubstituted BCBs via directed metalation of readily accessed BCB amides; this straightforward late stage approach generates a wide variety of bridge-substituted BCBs that can be easily converted into other useful small ring building blocks. Access to a monodeuterated BCB afforded unprecedented insight into the mechanism of dihalocarbene insertion into BCBs to afford bicyclo[1.1.1]pentanes (BCPs).
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