110590-29-9Relevant articles and documents
Direct evidence for a ruthenium(IV) oxo complex-mediated oxidation of a hydroxamic acid in the presence of phosphine oxide donors
Flower,Lightfoot,Wan,Whiting
, p. 1812 - 1813 (2001)
Ruthenium(II) complexes can be used to oxidise N-Boc hydroxylamine in the presence of tert-butylhydroperoxide to the corresponding nitroso dienophile, which is trapped using cyclohexa-1,3-diene as the hetero-Diels-Alder adduct; direct evidence has been obtained for the intervention of a triphenylphosphine oxide-stabilised ruthenium(IV) oxo-complex as the catalytically active species.
The development and application of ruthenium catalysed oxidations of a hydroxamic acid and in situ Diels-Alder trapping of the acyl nitroso derivative
Flower, Kevin R.,Lightfoot, Andrew P.,Wan, Hayley,Whiting, Andrew
, p. 2058 - 2064 (2002)
Ruthenium(II) complexes can be used to oxidise N-Boc-hydroxylamine in the presence of tert-butyl hydroperoxide (TBHP) to the corresponding nitroso dienophile, which is trapped by cyclohexa-1,3-diene as the hetero-Diels-Alder adduct. Direct evidence has been obtained for the intervention of a triphenylphosphine oxide-stabilised ruthenium(IV) oxo-complex as the catalytically active species. Use of a chiral bidentate bis-phosphine derived ruthenium ligand (BINAP or PROPHOS) results in very low asymmetric induction (8 and 11%). Ruthenium(II) salen complexes also catalyse the oxidation of N-Boc-hydroxylamine in the presence of TBHP, to give the N-Boc-nitroso compound which can be efficiently trapped with a range of dienes. However, use of an enantiopure ruthenium salen complex does not produce asymmetric induction via the trapping of the intermediate acyl nitroso dienophile with cyclohexadiene, which strongly suggests that the intermediate dissociates readily from the chiral ruthenium complex involved in the oxidation step prior to Diels-Alder cycloaddition.
The oxidative acylnitroso hetero-diels-alder reaction catalyzed by dirhodium caprolactamate
Tusun, Xiarepati,Lu, Chong-Dao
, p. 1801 - 1804 (2012)
An effective protocol is described for the generation and in situ Diels-Alder trapping of acylnitroso derivatives. In this procedure, the oxidation of hydroxamic acid is efficiently catalyzed by dirhodium(II) caprolactamate with tert-butyl hydroperoxide (
Hydroxyamination of aryl C-H bonds with N-hydroxycarbamate by synergistic Rh/Cu catalysis at room temperature
Yang, Wei,Sun, Jiaqiong,Xu, Xianxiu,Zhang, Qian,Liu, Qun
supporting information, p. 4420 - 4422 (2014/04/17)
A novel hydroamination of aryl C-H bonds has been accomplished using N-Boc-hydroxyamine via synergistic combination of rhodium and copper catalysis. The merger of two robust catalytic systems has allowed for the development of a mild and sustainable protocol for the direct formation of benzo[c]isoxazol-3(1H) -ones. This journal is the Partner Organisations 2014.
Copper-catalyzed aerobic oxidation of N-substituted hydroxylamines: Efficient and practical access to nitroso compounds
Frazier, Charles P.,Bugarin, Alejandro,Engelking, Jarred R.,Read De Alaniz, Javier
experimental part, p. 3620 - 3623 (2012/09/08)
A general and efficient aerobic oxidation of N-substituted hydroxylamines is described. The mild reaction conditions employed provide a catalytic and sustainable alternative to stoichiometric oxidation methods to gain access to a range of nitroso compound
Syntheses of structurally diverse amino acids, including δ-hydroxylysine, using the acyl nitroso Diels-Alder reaction
Bollans, Lee,Bacsa, John,O'Farrell, Daniel A.,Waterson, Scott,Stachulski, Andrew V.
supporting information; experimental part, p. 2160 - 2163 (2010/06/14)
By virtue of its ability to introduce amino and hydroxy functionalities in a 1,4-relationship with fully controlled relative stereochemistry, the acyl nitroso Diels-Alder (ANDA) reaction is ideally suited to the synthesis of structurally diverse, includin
Efficient cleavage of the N-O bond of 3,6-dihydro-1,2-oxazines mediated by some α-hetero substituted carbonyl compounds in mild conditions
Galvani, Gilles,Calvet, Geraldine,Blanchard, Nicolas,Kouklovsky, Cyrille
scheme or table, p. 1063 - 1070 (2009/02/05)
The efficient cleavage of the N-O bond of some nitroso Diels-Alder cycloadducts has been achieved in mild conditions, mediated either by 2,2-dimethyl-1,3-dioxan-5-one or 1,3-dithiolane-2-carboxaldehyde. These new and purely organic conditions allow an exc
Copper-catalyzed allylic hydroxyamination and amination of alkenes with Boc-hydroxylamine
Kalita, Biswajit,Nicholas, Kenneth M.
, p. 1451 - 1453 (2007/10/03)
Olefins react regioselectively with Boc-NHOH in the presence of Cu(I,II) salts to produce allyl-N(OH)(Boc) derivatives, apparently via the intermediacy of Boc-NO; yields and rates are dramatically improved by the addition of H 2O2. The corresponding allylamine derivatives, allyl-NH(Boc), are formed selectively from Boc-NHOH/olefin with CuBr/P(OEt) 3.
Generation of acyl nitroso compounds by the oxidation of N-acyl hydroxylamines with the Dess-Martin periodinane
Jenkins, Neil E.,Ware Jr., Roy W.,Atkinson, Robert N.,King, S. Bruce
, p. 947 - 953 (2007/10/03)
The oxidation of hydroxamic acids, N-hydroxyureas and N- hydroxycarbamates with the Dess-Martin periodinane generates the corresponding acyl nitroso compounds that react with conjugated dienes to produce the corresponding cycloadducts.
α-iodocycloalkenones: Synthesis of (±)-epibatidine
Sirisoma, Nilantha S.,Johnson, Carl R.
, p. 2059 - 2062 (2007/10/03)
A synthesis of the non-opiate analgesic alkaloid epibatidine was achieved in 13 steps and 13% Overall yield starting from 1,3-cyclohexadiene using in a key step a modified Stille coupling reaction on an α- iodocyclohexenone.
