Enantioselective Copper-Catalyzed Methylboration of Alkenes

Enantioselective Copper-Catalyzed Methylboration of Alkenes

An enantioselective Cu-catalyzed borylative cross-coupling reaction of alkenes, bis­(pinacolato)­diboron (B2(pin)2), and methyl iodide is reported. Alkenes including styrenes, β-substituted styrenes, and challenging aliphatic olefins were smoothly transferred to the desired methylboration products w...

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Veröffentlicht in:Organic letters 2018-03, Vol.20 (5), p.1346-1349
Hauptverfasser: Chen, Bin, Cao, Peng, Liao, Yang, Wang, Min, Liao, Jian
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creator Chen, Bin
Cao, Peng
Liao, Yang
Wang, Min
Liao, Jian
description An enantioselective Cu-catalyzed borylative cross-coupling reaction of alkenes, bis­(pinacolato)­diboron (B2(pin)2), and methyl iodide is reported. Alkenes including styrenes, β-substituted styrenes, and challenging aliphatic olefins were smoothly transferred to the desired methylboration products with excellent diastereoselectivities (dr up to >99:1) and enantioselectivities (er up to 99:1). The utility of this process was demonstrated by the synthesis of naproxen and formal synthesis of two natural products.
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title Enantioselective Copper-Catalyzed Methylboration of Alkenes
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