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Enantioselective Bromination of Silyl Enol Ethers with Chiral Pentacarboxycyclopentadienyl Bromide

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Chiral pentacarboxycyclopentadienyl bromide reagents were synthesized to accomplish enantioselective bromination of silyl enol ethers to give corresponding α-bromoketone products in good yields and up to 77% ee. A catalytic version… Click to show full abstract

Chiral pentacarboxycyclopentadienyl bromide reagents were synthesized to accomplish enantioselective bromination of silyl enol ethers to give corresponding α-bromoketone products in good yields and up to 77% ee. A catalytic version of this reaction was also demonstrated through the combination of Lewis acid activators and diethyl 2,2-dibromomalonate as stoichiometric achiral bromine source.

Keywords: chiral pentacarboxycyclopentadienyl; silyl enol; pentacarboxycyclopentadienyl bromide; enantioselective bromination; enol ethers; bromination silyl

Journal Title: Synlett
Year Published: 2023

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