期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 6, 页码 2397-2403出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja410220w
关键词
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资金
- National Institute of General Medical Sciences, National Institutes of Health [GM-36770]
- NIH [HL-25848]
- UCLA Graduate Division
- NIH Chemistry-Biology Interface Research Training Grant (USPHS National Research Service Award) [GM-008469]
- Royal Society [RG 110617]
- Oxford University Press John Fell Fund
- NSF
- National Science Foundation [OCI-1053575]
The intramolecular Diels-Alder reactions of cycloalkenones and terminal dienes occur with high endo stereoselectivity, both thermally and under Lewis-acidic conditions. Through computations, we show that steric repulsion and tether conformation govern the selectivity of the reaction, and incorporation of either BF3 or alpha-halogenation increases the rate of cycloaddition. With a longer tether, isomerization from a terminal diene to the more stable internal diene results in a more facile cycloaddition.
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