1185154-68-0Relevant academic research and scientific papers
An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations
Richmond, Edward,Ling, Kenneth B.,Duguet, Nicolas,Manton, Lois B.,elebi-?lcüm, Nihan,Lam, Yu-Hong,Alsancak, Sezen,Slawin, Alexandra M. Z.,Houk,Smith, Andrew D.
, p. 1807 - 1817 (2015/02/19)
The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.
Chiral scandium(III)-catalyzed enantioselective α-arylation of N-unprotected 3-substituted oxindoles with diaryliodonium salts
Guo, Jing,Dong, Shunxi,Zhang, Yulong,Kuang, Yulong,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information, p. 10245 - 10249 (2013/10/21)
Catalytic asymmetric α-arylation of N-unprotected 3-substituted oxindoles with diaryliodonium salts has been realized by a chiral Lewis acid promoted electrophilic addition and aryl-rearrangement process. Single C3-arylated products containing a quaternary carbon center were generated in high enantioselectivity and reactivity. Copyright
Pericyclic cascade with chirality transfer: Reaction pathway and origin of enantioselectivity of the hetero-claisen approach to oxindoles
Celebi-Oelcuem, Nihan,Lam, Yu-Hong,Richmond, Edward,Ling, Kenneth B.,Smith, Andrew D.,Houk, Kendall N.
, p. 11478 - 11482 (2012/01/06)
A new pericyclic cascade is proposed for the chiral auxiliary-controlled synthesis of 3,3-disubstituted oxindoles from nitrones and ketenes. The remarkable acyclic 1,6-stereochemical induction, hitherto unexplained, is rationalized by a stereoselective 3+
New chiral N-heterocyclic carbene ligands in palladium-catalyzed α-arylations of amides: Conformational locking through allylic strain as a device for stereocontrol
Jia, Yi-Xia,Katayev, Dmitry,Bernardinelli, Gerald,Seidel, Thomas M.,Kuendig, E. Peter
scheme or table, p. 6300 - 6309 (2010/07/14)
New Enders/Herrmann-type chiral N-heterocyclic carbene (NHC) ligands have been developed and applied in asymmetric palladium-catalyzed intramolecular α-arylations of amides. The best ligands feature the bulky tert-butyl group and ortho-substituted aryl gr
An asymmetric hetero-claisen approach to 3-alkyl-3-aryloxindoles
Duguet, Nicolas,Slawin, Alexandra M.Z.,Smith, Andrew D.
supporting information; experimental part, p. 3858 - 3861 (2009/12/05)
The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).
Bulky chiral carbene ligands and their application in the palladium- catalyzed asymmetric intramolecular α-arylation of amides
Kuendig, E. Peter,Seidel, Thomas M.,Jia, Yi-Xia,Bernardinelli, Gerald
, p. 8484 - 8487 (2008/09/18)
(Chemical Equation Presented) Bring on the big cats: New, C 2-symmetric bulky N-heterocyclic carbene ligands bring major improvements in the palladium-catalyzed asymmetric intramolecular α-arylation of amides to give oxindoles (see picture, dba=trans,trans- dibenzylideneacetone), which are formed in high yield and excellent enantiomeric purity.
