- Catalytic Enantioselective Nitroso Diels-Alder Reaction
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The nitroso Diels-Alder (NDA) reaction is an attractive strategy for the synthesis of 3,6-dihydro-1,2-oxazines and 1-amino-4-hydroxy-2-ene derivatives. Herein we report the Cu(I)-DTBM-Segphos catalyzed asymmetric intermolecular NDA reaction of variously substituted cyclic 1,3-dienes using highly reactive nitroso compounds derived from pyrimidine and pyridazine derivatives. In most of the cases studied, the cycloadducts were obtained in high yields (up to 99%) with very high regio-, diastereo-, and enantioselectivities (up to regioselectivity > 99:1, d.r. > 99:1, and >99% ee). As an application of this methodology, formal syntheses of conduramine A-1 and narciclasine were accomplished.
- Maji, Biplab,Yamamoto, Hisashi
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supporting information
p. 15957 - 15963
(2016/01/09)
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- SYNTHESIS AND PROPERTIES OF PHENYL(METHYL)-SUBSTITUTED 2- AND 4-NITROSOPYRIMIDINES
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Phenyl(methyl)-substituted 2- and 4-nitroso- and azoxypyrimidines were synthesized for the first time by the oxidation of phenyl(methyl)-substituted 2- and 4-hydroxyaminopyrimidines by activated MnO2, Ag2CO3 on zeolite, or BaMnO4.Certain chemical properti
- Moskalenko, G. G.,Sedova, V. F.,Mamaev, V. P.
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p. 805 - 811
(2007/10/02)
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- SYNTHESIS OF SUBSTITUTED 2- AND 4-HYDROXYAMINOPYRIMIDINES
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The reaction of 2- and 4-chlorine-containing alkyl(aryl)pyrimidines with hydroxylamine was studied.It was shown that, depending on the amount of hydroxylamine , N,O-dipyrimidinylhydroxyamides or the corresponding 2- and 4-hydroxyaminopyrimidines are formed together with 2- and 4-oxodihydropyrimidines.
- Moskalenko, G. G.,Sedova, V. F..,Mamaev, V. P.
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p. 1232 - 1236
(2007/10/02)
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