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- W2902030503 abstract "The origins of π-facial selectivities in the borohydride reduction of endocyclic iminium ions have been elucidated by density functional theory calculations. In reductions of conjugated (thermodynamic) iminium ions, the π-facial preference of the hydride attack was found to be due to torsional steering. Attack at the favored π-face leads to a lower-energy half-chair-like conformation of the tetrahydropyridine product, whereas attack at the other π-face results in an unfavorable twist-boat conformation. In reductions of nonconjugated (kinetic) iminium ions, torsional distinction is small between the top- and bottom-face attacks, and the π-facial selectivity of the hydride approach is primarily due to steric hindrance." @default.
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- W2902030503 date "2018-12-05" @default.
- W2902030503 modified "2023-10-13" @default.
- W2902030503 title "π-Facial Selectivities in Hydride Reductions of Hindered Endocyclic Iminium Ions" @default.
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- W2902030503 doi "https://doi.org/10.1021/acs.joc.8b02603" @default.
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