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Synfacts 2022; 18(10): 1093
DOI: 10.1055/s-0042-1752966
Metals in Synthesis

Stereospecific Functionalization of Activated Alkylboronic Esters under Copper Catalysis

Rezensent(en):
Martin Oestreich
,
Hendrik F. T. Klare
,
Lucie Finck
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
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Key words

alkyllithium - boronic esters - copper catalysis - stereospecific cross-coupling

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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