TY - JOUR T1 - Catalytic enantioselective amide allylation of isatins and its application in the synthesis of 2-oxindole derivatives spiro-fused to the α-methylene-γ-butyrolactone functionality. AU - Takahashi,Masaki, AU - Murata,Yusuke, AU - Yagishita,Fumitoshi, AU - Sakamoto,Masami, AU - Sengoku,Tetsuya, AU - Yoda,Hidemi, Y1 - 2014/07/22/ PY - 2014/05/28/received PY - 2014/7/23/entrez PY - 2014/7/23/pubmed PY - 2015/6/10/medline KW - allylation KW - antitumor agents KW - asymmetric catalysis KW - lactones KW - spiro compounds SP - 11091 EP - 100 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 35 N2 - This article is a full account of the work exploring the potential utility of catalytic enantioselective amide allylation of various isatins using indium-based chiral catalysts. A survey of various isatin substrates and NH-containing stannylated reagents revealed that the reaction has a remarkably wide scope to result in extremely high yields and enantioselectivities (up to >99 %, 99 % ee) of variously substituted homoallylic alcohols. Several mechanistic investigations demonstrated that the substrate-reagent hydrogen-bond interaction plays a critical role in the formation of the key transition states to result in enhanced catalytic reaction. The success of this approach allowed convenient access to chiral 2-oxindoles spiro-fused to the α-methylene-γ-butyrolactone functionality and their halogenated derivatives in almost enantiopure forms, thus highlighting the general utility of this synthetic method to deliver a large variety of antineoplastic drug candidates and pharmaceutically meaningful compounds. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25049083/Catalytic_enantioselective_amide_allylation_of_isatins_and_its_application_in_the_synthesis_of_2_oxindole_derivatives_spiro_fused_to_the_α_methylene_γ_butyrolactone_functionality_ DB - PRIME DP - Unbound Medicine ER -