203176-20-9Relevant academic research and scientific papers
Neighbouring group assisted sulfonamide cleavage of sharpless aminols under acetonation conditions
Chandrasekhar,Mohapatra, Suchismita
, p. 695 - 698 (1998)
It is accidentally observed that N-Ts cleavage and simultaneous protection of resulting free amino group as acetonide with the adjacent hydroxy group is achieved in one pot. Neighbouring carboxylic ester group is essential for this transformation.
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.
supporting information, 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.
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.
supporting information; experimental part, 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+
Pyridine-N-oxide as a mild reoxidant which transforms osmium-catalyzed oxidative cyclization
Donohoe, Timothy J.,Wheelhouse, Katherine M. P.,Lindsay-Scott, Peter J.,Glossop, Paul A.,Nash, Ian A.,Parker, Jeremy S.
, p. 2872 - 2875 (2008/12/23)
(Chemical Equation Presented) The PNOman can: The use of pyridine-N-oxide (PNO) transforms the catalytic oxidative cyclization to include the formation of pyrrolidines from N-Z-protected amino alcohols and amino acids (see scheme; Z = PhCH2OCO). This new method expands the scope of the oxidative cyclization as illustrated with the synthesis of a range of di- and trisubstituted pyrrolidines with complete control of stereochemistry.
