Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides
Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.
Kong, Chen,Driver, Tom G.
supporting information
p. 802 - 805
(2015/04/27)
Promoting reductive tandem reactions of nitrostyrenes with Mo(CO)6 and a palladium catalyst to produce 3 h -indoles
The combination of Mo(CO)6 and 10 mol % of palladium acetate catalyzes the transformation of 2-nitroarenes to 3H-indoles through a tandem cyclization-[1,2] shift reaction of in situ generated nitrosoarenes. Mo(CO)6 appears to have dual roles in this transformation: generate CO and promote C-N bond formation to increase the yield of the N-heterocycle product.
Jana, Navendu,Zhou, Fei,Driver, Tom G.
supporting information
p. 6738 - 6741
(2015/06/16)
Total synthesis of (±)-paroxetine by diastereoconvergent cobalt-catalysed arylation
A total synthesis of paroxetine is reported, with a diastereoselective and diastereoconvergent cobalt-catalysed sp3-sp2 coupling reaction involving a 3-substituted 4-bromo-N-Boc-piperidine (Boc = tert-butoxycarbonyl) substrate as a key step. A 9:1 diastereoselectivity was obtained, while a control experiment involving a conformationally locked 3-substituted 4-bromo-tert-butyl cyclohexane ring proceeded with essentially complete stereoselectivity.
Despiau, Carole F.,Dominey, Andrew P.,Harrowven, David C.,Linclau, Bruno
supporting information
p. 4335 - 4341
(2014/07/21)
Highly diastereoselective formation of spirocyclic compounds via 1,5-hydrogen transfer: A total synthesis of (-)-erythrodiene
(Chemical Equation Presented) A highly stereoselective synthesis of (-)-erythrodiene starting from 4-isopropylcyclohexanone is described. The key reactions are an asymmetric methoxycarbonylation of the starting ketone and a highly diastereoselective radical cascade involving addition of a phenylthiyl radical to a terminal alkyne followed by a 1,5-hydrogen transfer and a 5-exo-cyclization.
Lachia, Mathilde,Denes, Fabrice,Beaufils, Florent,Renaud, Philippe
p. 4103 - 4106
(2007/10/03)
Kinetics of Decarboxylation of the Two Epimers of 5-tert-Butyl-1-methyl-2-oxocyclohexanecarboxylic Acid: Lack of Stereoelectronic Control in β-Keto Acid Decarboxylation
Rates of decarboxylation of the two epimers of 5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylic acid have been measured under both acidic and basic conditions at 25 deg C.The decomposition of isomer 1e (methyl and tert-butyl trans) is more rapid than that
Kayser, Robert H.,Brault, Margaret,Pollack, Ralph M.,Bantia, Shanta,Sadoff, Scott F.
p. 4497 - 4502
(2007/10/02)
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