A practical access to fluoroalkylthio(seleno)-functionalized bicyclo[1.1.1]pentanes

Rational design of new bioisosteres through introduction of high-value functional groups to bicyclo[1.1.1]pentane (BCP) is of particular use for drug discovery. Disclosed herein is the first access to valuable fluoroalkylthio(seleno)-functionalized BCPs. A range of SCF 3 , SCF 2 H, SCFH 2 , SeCF 3 ,...

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Veröffentlicht in:Science China. Chemistry 2020-08, Vol.63 (8), p.1025-1029
Hauptverfasser: Wu, Zhen, Xu, Yaohui, Liu, Jige, Wu, Xinxin, Zhu, Chen
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Sprache:eng
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Zusammenfassung:Rational design of new bioisosteres through introduction of high-value functional groups to bicyclo[1.1.1]pentane (BCP) is of particular use for drug discovery. Disclosed herein is the first access to valuable fluoroalkylthio(seleno)-functionalized BCPs. A range of SCF 3 , SCF 2 H, SCFH 2 , SeCF 3 , SeC 4 F 9 , and SeC 8 F 17 groups are readily incorporated to BCPs under mild conditions. Concomitant installation of a sulfone provides a platform for incorporation of the BCP motif to bioactive molecules. This practical protocol features novel BCP scaffolds, broad substrate scope, excellent atom-economy, simple operation, and gram-scale preparation.
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-020-9733-y