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Synfacts 2022; 18(10): 1093
DOI: 10.1055/s-0042-1752966
DOI: 10.1055/s-0042-1752966
Metals in Synthesis
Stereospecific Functionalization of Activated Alkylboronic Esters under Copper Catalysis
Xu N,
Liang H,
Morken JP.
*
Boston College, Chestnut Hill, USA
Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.
J. Am. Chem. Soc. 2022;
144: 11546-11552
DOI: 10.1021/jacs.2c04037
Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.
J. Am. Chem. Soc. 2022;
144: 11546-11552
DOI: 10.1021/jacs.2c04037
Significance
A copper-catalyzed method for the stereospecific functionalization of boron ‘ate’ complexes obtained from enantioenriched pinacol boronic esters and tert-butyllithium is disclosed. This protocol is operationally simple and can be carried out on gram scale.
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Comment
The tert-butyl-activated boronate complexes undergo stereoretentive transmetalation to copper cyanide and subsequent coupling with various electrophiles such as allyl-, alkynyl-, propargyl- and acyl halides, β-haloenones and hydroxylamine esters.
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Publikationsverlauf
Artikel online veröffentlicht:
20. September 2022
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