期刊
CHEMICAL SCIENCE
卷 6, 期 8, 页码 4912-4922出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc01614b
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资金
- National University of Singapore [R-143-000-599-112]
- GSK-EDB [R-143-000-491-592]
- Ministry of Education (MOE) of Singapore [R-143-000-494-112]
Phosphine-catalyzed highly enantioselective gamma-additions of 5H-thiazol-4-ones and 5H-oxazol-4-ones to allenoates have been developed for the first time. With the employment of amino-acid derived bifunctional phosphines, a wide range of substituted 5H-thiazol-4-one and 5H-oxazol-4-one derivatives bearing heteroatom (S or O)-containing tertiary chiral centers were constructed in high yields and excellent enantioselectivities. The reported method provides facile access to enantioenriched tertiary thioethers/alcohols. The mechanism of the gamma-addition reaction was investigated by performing DFT calculations, and the hydrogen bonding interactions between the Bronsted acid moiety of the phosphine catalysts and the C=O unit of the donor molecules were shown to be crucial in asymmetric induction.
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