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ORGANIC LETTERS
卷 17, 期 24, 页码 6058-6061出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03072
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资金
- Hong Kong RGC [GRF604513, M-HKUST607/12, ECS605812]
The first catalytic asymmetric intermolecular alcohol conjugate addition to o-quinone methides (o-QMs) is disclosed. Due to reversible C-O bond formation and low nucleophilicity of alcohols, catalytic asymmetric oxa-Michael additions with simple alcohol nucleophiles to establish acyclic oxygenated carbon stereocenters remain scarce. The present reaction represents a rare example of this type. With a suitable chiral acid catalyst, the in situ formation of o-QMs and subsequent conjugate addition proceeded with high efficiency and enantioselectivity. The chiral ether products are versatile precursors to other chiral molecules.
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