期刊
ORGANIC LETTERS
卷 16, 期 24, 页码 6362-6365出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol5031537
关键词
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资金
- NIH-NIGMS [R01 GM080269]
- Caltech
- American Chemical Society Division of Organic Chemistry
- NSF CRIF:MU
- NIH [RR027690]
A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H is reported. The all-carbon quaternary stereocenter was constructed by asymmetric conjugate addition catalyzed by a palladium(II) (S)-tert-butylpyridinooxazoline complex. The unexpected formation of a [3.2.1] bicyclic intermediate required the identification of a new route. Analysis of the Hammett constants for para-substituted arenes enabled the rational design of a highly enantioselective conjugate addition substrate that led to the completion of the formal synthesis.
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