842123-78-8Relevant articles and documents
Mechanistic dichotomy in the asymmetric allylation of aldehydes with allyltrichlorosilanes catalyzed by chiral pyridine N-oxides
Malkov, Andrei V.,Stoncius, Sigitas,Bell, Mark,Castelluzzo, Fabiomassimo,Ramirez-Lopez, Pedro,Biedermannova, Lada,Langer, Vratislav,Rulisek, Lubomir,Kocovsky, Pavel
, p. 9167 - 9185 (2013/07/26)
Detailed kinetic and computational investigation of the enantio- and diastereoselective allylation of aldehydes 1 with allyltrichlorosilanes 5, employing the pyridine N-oxides METHOX (9) and QUINOX (10) as chiral organocatalysts, indicate that the reaction can proceed through a dissociative (cationic) or associative (neutral) mechanism: METHOX apparently favors a pentacoordinate cationic transition state, while the less sterically demanding QUINOX is likely to operate via a hexacoordinate neutral complex. In both pathways, only one molecule of the catalyst is involved in the rate- and selectivity-determining step, which is supported by both experimental and computational data. Copyright
Synthesis of axially chiral C10-BridgePHOS oxides and their use as organocatalysts in enantioselective allylations of aldehydes
Chen, Jianzhong,Liu, Delong,Fan, Dongyang,Liu, Yangang,Zhang, Wanbin
, p. 8161 - 8168 (2013/09/02)
A series of C10-BridgePHOS oxides possessing different substituted groups on the diphenyl phosphine system were synthesized and tested as organocatalysts in the allylation of aldehydes with allyltrichlorosilane, providing chiral homoallylic alc
Development of chiral dinitrones as modular Lewis base catalysts: Asymmetric allylation of aldehydes with allyltrichlorosilanes
Seon Oh, Young,Kotani, Shunsuke,Sugiura, Masaharu,Nakajima, Makoto
experimental part, p. 1833 - 1835 (2010/11/05)
Chiral dinitrones were synthesized by the condensation of a C 2-symmetrical chiral dihydroxylamine with various aldehydes. The electronic and steric properties of the dinitrones can be modified by changing the aldehyde component. The activity o
On the mechanism of asymmetric allylation of aldehydes with allyltrichlorosilanes catalyzed by QUINOX, a chiral isoquinoline N-oxide
Malkov, Andrei V.,Ramirez-Lopez, Pedro,Biedermannova, Lada,Rulisek, Lubomir,Dufkova, Lenka,Kotora, Martin,Zhu, Fujiang,Kocovsky, Pavel
, p. 5341 - 5348 (2008/12/21)
Allylation of aromatic aldehydes 1a-m with allyl- and crotyl- trichlorosilanes 2-4, catalyzed by the chiral N-oxide QUINOX (9), has been found to exhibit a significant dependence on the electronics of the aldehyde, with p-(trifluoromethyl)benzaldehyde 1g
New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes
Malkov, Andrei V.,Westwater, Mary-Margaret,Gutnov, Andrey,Ramírez-López, Pedro,Friscourt, Frédéric,Kadl?íková, Aneta,Hoda?ová, Jana,Rankovic, Zoran,Kotora, Martin,Ko?ovsky, Pavel
scheme or table, p. 11335 - 11348 (2009/04/11)
Asymmetric allylation of aromatic aldehydes 1 with allyltrichlorosilane (2) can be catalyzed by new terpene-derived bipyridine N,N′-dioxides 12-15 and an axially chiral biisoquinoline dioxide 17b with good enantioselectivities. Dioxides have been found to be more reactive catalysts than their monooxide counterparts. Crown Copyright
