799561-07-2Relevant academic research and scientific papers
3-alkenyl-2-silyloxyindoles: An enabling, yet understated progeny of vinylogous carbon nucleophiles
Rassu, Gloria,Zambrano, Vincenzo,Tanca, Rossella,Sartori, Andrea,Battistini, Lucia,Zanardi, Franca,Curti, Claudio,Casiraghi, Giovanni
, p. 466 - 470 (2012)
We introduce novel 3-alkenyl-2-silyloxyindole nucleophiles and demonstrate their utility by developing an unprecedented vinylogous Mukaiyama-type aldol reaction with aromatic aldehydes. This reaction displays excellent levels of γ-site selectivity and dia
Regio- and diastereoselective vinylogous Mannich addition of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines
Liu, Yingle,Yang, Yi,Huang, Yangen,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 67 - 72 (2015/02/19)
An efficient asymmetric vinylogous Mannich (AVM) addition reaction of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines has been developed. This reaction provided various optical active α-alkylidene-δ-amino-δ-fluoroalkyl oxindoles in excellent yields, complete γ-site regioselectivity, and excellent diastereoselectivities.
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).
