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- W2109136695 abstract "The stereodivergent facial differentiation of the intermolecular hetero Diels-Alder reaction of the 1-oxa-1,3-butadiene 1 with 2 in the presence of trimethylsilyl trifluoromethanesulfonate (TMS-OTf) or Me2AlCl is explained on the basis of semiempirical calculations (AM1 and PM3). The oxabutadiene 9 was shown to prefer the anti arrangement of the carbonyl groups of the imide moiety in the ground state by 1.8 kcal/mol (Am1) or 2.2 kcal/mol (PM3). In the silylated compound 10 this preference is even more pronounced. In contrast, in the chelate 11 the imide moiety is fixed in a syn conformation. The orientation of the oxazolidinone rings in 10 and 11 is opposite: thus, the absolute configuration of the cycloadducts is determined by a facial differentiation due to an asymmetric induction under chelate control (11) or nonchelate control (10)." @default.
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- W2109136695 date "1995-11-01" @default.
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- W2109136695 title "Molecular switches: Calculations on the stereodivergent hetero Diels-Alder reaction of chiral 1-oxa-1,3-butadienes with different lewis acids" @default.
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- W2109136695 doi "https://doi.org/10.1002/jlac.1995199511271" @default.
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