期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 24, 页码 12058-12075出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02037
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资金
- Australian government
- Australian Research Council [DP0451189]
- Gates Millennium Scholarship Program
- National Institute of General Medical Sciences
- National Institutes of Health [GM 36700]
- German Academic Exchange Service (DAAD)
- Australian Research Council [DP0451189] Funding Source: Australian Research Council
The intramolecular Diels-Alder reaction has been used as a powerful method to access the tricyclic core of the eunicellin natural products from a number of 9-membered-ring precursors. The endo/exo selectivity of this reaction can be controlled through a remarkable organocatalylic approach, employing MacMillan's imidazolidinone catalysts, although the mechanistic origin of this selectivity remains unclear. We present a combined experimental and density functional theory investigation, providing insight into the effects of medium-ring constraints on the organocatalyzed intramolecular Diels-Alder reaction to form the isobenzofuran core of the eunicellins.
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