Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition

Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stereoselectivity. The method works best for tertiary and secondary alkyl iodides. The Z-vinyl boronate products are easily converted to other Z-alkenes by transformation of the boronate group. The method is applied for the formal total synthesis of a 5-HT2c receptor agonist.


Published in:
Organic Letters, 21, 2, 490-493
Year:
Jan 18 2019
ISSN:
1523-7060
1523-7052
Keywords:
Laboratories:


Note: The file is under embargo until: 2020-01-17


 Record created 2019-02-08, last modified 2019-08-15

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