- Ru-Catalyzed Asymmetric Hydrogenative/Transfer Hydrogenative Desymmetrization of Meso-Epoxy Diketones
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Via a strategy of asymmetric reductive desymmetrization, chiral cis-epoxy naphthoquinols with multiple contiguous stereocenters and functional groups were synthesized with excellent enantioselectivities (96-99% ee) and diastereoselectivities (8/1-15/1). A combined asymmetric hydrogenation/transfer hydrogenation mechanism was proposed based on experimental results.
- Hong, Yuping,Chen, Jianzhong,Zhang, Zhenfeng,Liu, Yangang,Zhang, Wanbin
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supporting information
p. 2640 - 2643
(2016/06/15)
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- Synthesis of 2,3-Dialkyl-6,7-dichloro- and 2,3-Dialkyl-6,7-dibromo-1,4-naphthoquinones
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Thermal treatment of 1,4-benzoquinone and its 2-methyl and 2,3-dimethyl homologues with 3,4-dichlorothiophene 1,1-dioxide followed by oxidation affords the corresponding 6,7-dichloro-1,4-naphthoquinones; the parent compound and its 2-methyl homologue can be alkylated at the free quinonoid positions using the alkanoic acid-persulphate-silver ion system.Nitration of 2,3-dibromonaphthalene yields 2,3-dibromo-5-nitronaphthalene, which via sequential reduction, diazotisation, hydrolysis, and oxidation with Fermy's salt gives 6,7-dibromo-1,4-naphthoquinone, which can be similarly alkylated.
- Ashnagar, Alamdar,Bruce, J. Malcolm,Lloyd-Williams, Paul
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p. 559 - 562
(2007/10/02)
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