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Base-Catalyzed Thiolysis of a,ß-Epoxy Ketones in Water. A Green Tool for the Synthesis of Target Compounds
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Cobalt(II)Chloride-Catalyzed Chemioselective Sodium Borohydride Reduction of Azides in Water
No full textNaOH-Catalyzed Thiolysis of alpha,beta-Epoxyketones in Water. A Key Step in the Synthesis of Target Molecules Starting from alpha,beta-Unsaturated Ketones
No full textNaOH (0.02-0.3 molar equiv) is an efficient catalyst for the thiolysis reactions of alpha,beta-epoxy ketones with alkyl and aryl thiols in water. Thiolysis of 3,4-epoxyheptan-2-one (1) with thiols 2a-d has been accomplished in mild conditions (30 °C and pH 6 or 9) with complete C-R-regioselectivity and anti-stereoselectivity, and the corresponding anti-beta-carbonyl-beta-hydroxysulfides 3a-d have been prepared in excellent yields (95-98%). Compounds 3a-d, depending on their nature and pH conditions, have undergone dehydration, C-3 epimerization reaction, and retroaldol condensation.
Dehydration of anti-3a-d has been chemoselectively carried out by in situ acidic treatment at
70 °C, giving stereoselectively the related (Z)-vinyl sulfides 4 in 89-94% overall yields. Under NaOHcatalyzed thiolysis conditions, cyclic alpha,beta-epoxyketones 6-9 have shown C-R attack only and spontaneously dehydrated to furnish the corresponding vinyl sulfides in high yields (90-96%). The reactions of calchone oxide (10) with thiols 2b-d have exclusively resulted in the formation of â-carbonylsulfides 10b-d (82-93% yield), coming from the nucleophilic attack at the R-position and retroaldol condensation. To highlight the synthetic utility of this procedure, one-pot multisteps preparation of vinyl sulfides 7b and 7c, vinyl sulfoxides 12 and 13, and 1,5,6,7-tetrahydro-4H-1,2,3-benzotriazol-4-one (14) starting from 2-cyclohexen-1-one (11) have also been reported
Lewis-Acid Catalyzed Organic Reactions in Water. The Case of AlCl3, TiCl4 and SnCl4 Belived to be Unusable in Aqueous Medium
No full textAlCl3, TiCl4 e SnCl4 come Acidi di Lewis Water-Tolerant nella Reazione di Azidolisi ed Alogenolisi di Acidi alfa,beta-Epossicarbossilici in Acqua -
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