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ALPHA,ALPHA'-DIOXOTHIONES .2. ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL NON-RACEMIC ALPHA,ALPHA'-DIOXOTHIONES

机译:阿尔法,阿尔法-二氧噻吩酮2。手性非自由基阿尔法,阿尔法-二氧杂环丁酮的不对称狄尔斯-阿尔德反应

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Chiral non-racemic alpha,alpha'-dioxothiones 2a-g and 17 are obtained from chiral beta-ketoesters using the phthalimidesulfenyl chloride 1 as key reagent. The ability of these thiones to discriminate between the enantiotopic faces of several dienophiles has been evaluated, The best diastereoisomeric excesses (67-80%) were obtained when the alpha-acyl thiones were involved as electron-poor dienes in inverse electron demand Diels-Alder reactions with electron-rich styrenes as dienophiles. The possibility to obtain thiones bearing two,chiral groups as-well as the reactions where the alpha-acyl thiones 2 participate as dienophiles are also shown. (C) 1997 Elsevier Science Ltd. [References: 22]
机译:手性非外消旋的α,α'-二氧噻吩类化合物2a-g和17是由邻苯二甲酰亚胺基氯化亚砜1作为关键试剂,从手性β-酮酸酯获得的。评估了这些硫酮区分几种亲二烯体的对映体表面的能力。当α-酰基硫酮作为逆电子需求的电子贫二烯参与时,可获得最佳非对映异构体过量(67-80%)。与富电子苯乙烯作为亲二烯体反应。还显示了获得带有两个手性基团的硫酮的可能性以及α-酰基硫酮2作为亲二烯体参与的反应。 (C)1997 Elsevier Science Ltd. [参考:22]

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