Rh2(OAc)4-Mediated Diazo Decomposition of -(N-Tosyl)amino- -keto- - diazo Carbonyl Compounds: A Novel Approach to Pyrrole Derivatives Synthesis of Pyrroles from Imine
نویسندگان
چکیده
Synlett 2002, No. 11, Print: 29 1
منابع مشابه
Synthesis of oxygen-containing heterocyclic compounds based on the intramolecular O–H insertion and Wolff rearrangement of a-diazocarbonyl compounds
The addition products of Ti(IV)-enolate derived from b-keto a-diazo carbonyl compound to ketones or a,b-unsaturated compounds were subjected to Rh2(OAc)4-catalyzed and photo-induced diazo decomposition. The Rh2(OAc)4-catalyzed reaction afforded intramolecular O–H insertion products, while the photo-induced reaction gave Wolff rearrangement/intramolecular nucleophilic addition products. The tran...
متن کامل1,2-migration in rhodium(II) carbene transfer reaction: remarkable steric effect on migratory aptitude.
A series of diazo carbonyl compounds bearing different substituents have been prepared in order to investigate the steric effect in 1,2-migration reaction of rhodium(II) carbene. Through the investigation on the diazo decomposition of these compounds with Rh2(OAc)4, it was found that the steric effect could dramatically influence the migratory aptitude. In many cases, the steric effect could ov...
متن کاملInvestigation of the transition-metal- and acid-catalyzed reactions of beta-(N-tosyl)amino diazo carbonyl compounds.
A series of beta-(N-tosyl)amino diazo carbonyl compounds have been prepared by nucleophilic condensation of N-tosylimines with acyldiazomethanes. The diazo decomposition of these diazo carbonyl compounds under various catalytic conditions, including Rh(II) carboxylates, Cu(I) and Cu(II) complexes, PhCO(2)Ag/Et(3)N, TsOH, and SnCl(2).2H(2)O, has been investigated. It was found that, in most case...
متن کاملA new method for the synthesis of 2-cyclopenten-1-one-5- carboxylic ester derivatives via Rh2(OAc)4-mediated intramolecular C–H insertion reaction of 4Z-b-vinyl-a-diazo b-ketoesters
2-Cyclopenten-1-one-5-carboxylic ester derivatives 14 are synthesized in a four-step-reaction sequence starting from alkynyl aldehydes 9 via 4Z-b-vinyl-a-diazo b-ketoesters intermediate 8. The synthetic method for 8 is described. When the d substituent is an alkyl group, Rh(II)-mediated decomposition of the diazo compounds 8 led to an intramolecular C–H insertion to afford 2-cyclopenten-1-one-5...
متن کامل1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition: a novel approach to alpha-aryl-beta-enamino esters.
N-Tosyl diazoketamines were prepared by addition of the ethyl alpha-diazoacetate anion to N-sulfonylimines. The diazo decomposition of the diazoketamines with Rh(2)(OAc)(4) complex resulted in aryl migration to give alpha-aryl-beta-enamino esters in good yields and high stereoselectivity. The effect of the catalysts on the migratory aptitude of 1,2-aryl over 1,2-hydride migration was studied. A...
متن کامل