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- W2117369615 abstract "It has been shown that dienophiles cycloadd selectively to one face of o-quinodimethanes (o-QDMs) bearing chiral α-alkoxy groups. The face selectivity (diastereoselectivity) increases for the series of chiral groups -OCH(Ph)CH 3 , -OCH(Ph)CH(CH 3 ) 2 , and -OCH(Ph)C(CH 3 ) 3 . A similar effect on the face selectivity of the Diels–Alder reactions of chiral alkoxy vinyl ethers for the same series of chiral groups has been noted previously by others. A mechanism has been proposed to explain the face selectivity in the cycloaddition reactions of the alkoxy o-QDMs. Abinitio molecular orbital calculations with geometry optimization on vinyl 1-phenylethyl ether to determine its lowest energy conformations support the proposed mechanism. The absolute stereochemistries of the o-QDM cycloadducts have been determined to verify the predictions of the model. Keywords: o-quinodimethanes, asymmetric, Diels–Alder, cycloaddition." @default.
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- W2117369615 date "1989-06-01" @default.
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- W2117369615 title "Asymmetric induction in Diels–Alder reactions of α-alkoxyorthoquinodimethanes" @default.
- W2117369615 doi "https://doi.org/10.1139/v89-153" @default.
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