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• W2952078574 abstract "Aryl-halo-diazirines react under basic conditions with 1,3-cis-, 1,2-cisand 1,2-trans-diols to give acetals. Yields are high. Diastereoselectivities depend upon the diol and upon the reaction conditions. Thus, reaction of the 1,3-cis-diol 1 (Scheme 1) with 2 gave 3 as a single diastereoisomer. The 1,2-cis-diols 4 and 7 led to the endo- and exo-acetals 5/6 (93:7) and 8/9 (ca.10:1), respectively, The 1,2-trans-diols 10, 16, and 19 reacted with 2 to afford 11/12 (90:10), 17/18 (1:1), and 20/21 (6:1), respectively. Reaction of the (4-nitrophenyl)diazirine 13 with 10 at higher temperatures yielded 14/15 (6:4). The uracil moiety, the acetamido group, and the enol-ether moiety are compatible with the reaction conditions. The diastereoselectivity is rationalized on the basis of a reaction sequence involving alkoxy-halogen exchange, which is regioselective or not, thermolysis of the ensuing alkoxydiazirine(s), protonation of the alkoxycarbene to form an (E)-configurated oxycarbenium ion, and attack of the neighboring oxy or hydroxy group, which is only possible for a limited range of conformers." @default.
• W2952078574 created "2019-06-27" @default.
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• W2952078574 date "1993-02-10" @default.
• W2952078574 modified "2023-10-16" @default.
• W2952078574 title "A New Synthesis of Benzylidene Acetals" @default.
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• W2952078574 doi "https://doi.org/10.1002/hlca.19930760115" @default.
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