1352790-93-2Relevant academic research and scientific papers
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 (2011)
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+
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.
Asymmetric pericyclic cascade approach to spirocyclic oxindoles
Richmond, Edward,Duguet, Nicolas,Slawin, Alexandra M. Z.,Lebl, Tomas,Smith, Andrew D.
supporting information; experimental part, p. 2762 - 2765 (2012/07/14)
The reaction of chiral N-arylnitrones with carbocyclic alkylarylketenes generates spirocyclic oxindoles in good yields and with excellent levels of enantioselectivity (90-99% ee) via a pericyclic cascade process.
