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- W4387392933 abstract "The diene-transmissive 2-fold Diels–Alder sequence between carbon-based dienophiles and [3]dendralenes is becoming an established method for polycarbocycle synthesis. Here, we demonstrate for the first time that imines are competent participants in intermolecular formal [4 + 2] cycloadditions with dendralenes. After a second Diels–Alder process with a carbadienophile, hexahydro- and octahydro-isoquinoline structures are formed. The formal aza-Diels–Alder reaction, which requires Lewis acid promotion, proceeds in high regio- and stereoselectivity under optimized conditions. ωB97XD/Def2-TZVP//M06-2X/6-31+G(d,p) calculations reveal a stepwise ionic mechanism for the formal aza-dienophile cycloadditions and also explain an unexpected Z → E olefin isomerization of a non-reacting C═C bond in the first formal cycloaddition." @default.
- W4387392933 created "2023-10-07" @default.
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- W4387392933 date "2023-10-06" @default.
- W4387392933 modified "2023-10-12" @default.
- W4387392933 title "A Rapid Aza-Bicycle Synthesis from Dendralenes and Imines" @default.
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- W4387392933 doi "https://doi.org/10.1021/acs.orglett.3c02890" @default.
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