期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 10, 页码 3310-3313出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b01445
关键词
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资金
- UC Irvine
- National Institutes of Health [GM105938]
- Eli Lilly
We report a Rh-catalyzed enantioselective cycloisomerization of alpha, omega-heptadienes to afford cyclohexenes bearing quaternary carbon centers. Rhodium(I) and a new SDP ligand promote chemoselective formation of a cydohex-3-enecarbaldehyde motif that is inaccessible by the Diels-Alder cycloaddition. Various alpha,alpha-bisallylaldehydes rearrange to generate six-membered rings by a mechanism triggered by aldehyde C-H bond activation. Mechanistic studies suggest a pathway involving regioselective carbometalation and endocyclic beta-hydride elimination.
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