799561-08-3Relevant academic research and scientific papers
Molybdenum-catalyzed asymmetric allylation of 3-alkyloxindoles: Application to the formal total synthesis of (-)-physostigmine
Trost, Barry M.,Zhang, Yong
, p. 4590 - 4591 (2006)
The first example of Mo-catalyzed asymmetric allylation for the generation of quaternary stereocenters at a prochiral nucleophile is reported. A variety of 3-alkyl oxindoles can be alkylated with high yields and enantioselectivity. This method provides expedited access to (-)-physostigmine and its analogues. Copyright
N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates
Thomson, Jennifer E.,Kyle, Andrew F.,Gallagher, Katherine A.,Lenden, Philip,Concellon, Carmen,Morrill, Louis C.,Miller, Andrew J.,Joannesse, Caroline,Slawin, Alexandra M. Z.,Smith, Andrew D.
experimental part, p. 2805 - 2818 (2009/04/04)
The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated. Georg Thieme Verlag Stuttgart.
Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine
Huang, Audris,Kodanko, Jeremy J.,Overman, Larry E.
, p. 14043 - 14053 (2007/10/03)
A versatile route to enantiopure 3,3-disubstituted oxindoles and 3a-substituted pyrrolidinoindolines is described in which diastereoselective dialkylation of enantiopure ditriflate 10 with oxindole enolates is the central step. These reactions are rare examples of alkylations of prostereogenic enolates with chiral sp3 electrophiles that proceed with high facial selectivity (10-20:1). The scope of this method is explored, and a model to rationalize the sense of stereoselection is advanced. This dialkylation chemistry was used to synthesize (-)-phenserine on a multigram scale in six steps and 43% overall yield from 5-methoxy-1,3-dimethyloxindole (27) and to complete a short formal total synthesis of (-)-physostigmine (2).
