期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 24, 页码 9511-9515出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b03653
关键词
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资金
- EU for H-2020 Marie Sklodowska-Curie Fellowship [744242]
- EPSRC [EP/R012695/1]
- Marie Curie Actions (MSCA) [744242] Funding Source: Marie Curie Actions (MSCA)
- EPSRC [EP/L011999/1, EP/R012695/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/L011999/1] Funding Source: researchfish
While radical additions to pi-bonds are well established, additions to sigma-bonds are far less explored. We have found that electron deficient radicals derived from alkyl iodides under visible light irradiation add to the central strained bond of bicyclobutyl (BCB)-boronate complexes and lead to 1,3-alkyl disubstituted cyclobutyl boronic esters in high yields, with full stereospecificity and high levels of stereoselectivity. Novel cyclobutyl-substituted structures, including peptide and steroid boronic ester derivatives can be accessed. Additionally, although the use of electron-rich alkyl iodides as radical precursors was found to be ineffective, an alternative route involving alkylsulfonylation of the BCB-boronate followed by reductive desulfonylation provided access to simple alkyl substituted cyclobutane products.
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