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Synfacts 2022; 18(11): 1201
DOI: 10.1055/s-0042-1753005
Metals in Synthesis

1,1-Difunctionalization of Terminal Alkenes to Chiral Allylboronates under Nickel Catalysis

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Benedikt Wolff
Sun C, Li Y, Yin G. * Wuhan University, P. R. of China
Practical Synthesis of Chiral Allylboronates by Asymmetric 1,1-Difunctionalization of Terminal Alkenes.

Angew. Chem. Int. Ed. 2022;
61: e202209076
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Key words

allylboronates - alkene difunctionalization - nickel catalysis

Significance

A method for the catalytic difunctionalization of terminal alkenes to form chiral allylboronates is presented. This enantioconvergent process relies on an α-selective β-hydride elimination as the key step.


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Comment

The products were formed in moderate to high yields and with high enantioselectivities. The utility of this method was further demonstrated by the rapid synthesis of key intermediates of complex drug molecules.


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Publication History

Article published online:
18 October 2022

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