Organic Letters p. 4030 - 4034 (2019)
Update date:2022-08-03
Topics:
Yamamoto, Eiji
Wakafuji, Kodai
Mori, Yusuke
Teshima, Gaku
Hidani, Yuki
Tokunaga, Makoto
Bifunctional phosphonium/thioureas derived from tert-leucine behaved as highly selective catalysts for enantioselective protonation of enol esters, providing α-chiral ketones in yields of up to 99% with high enantioselectivities (up to 98.5:1.5 er). Control experiments clarified that a bulky tert-butyl group and phosphonium and thiourea moieties were necessary to achieve such high stereoselectivity. In addition, mechanistic investigations indicated the catalyst was converted to the corresponding betaine species, which served as a monomolecular catalyst.
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