新型3-季碳胺甲基氧化吲哚类化合物的高效合成
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摘要
以3-取代氧化吲哚为起始原料,TBAB为相转移催化剂,与亚胺前体经Mannich反应高效合成了11个新型的3-季碳胺甲基氧化吲哚,收率68%~98%,其结构经1H NMR,13C NMR和HR-ESI-MS表征。
Eleven novel quaternary 3-aminomethyl oxindole compounds,in yield of 68% ~ 98%,were efficiently synthesized by Mannich reaction of 3-substituted oxindoles with imine precursors,using TBAB as the phase transfer catalyst. The structures were characterized by1 H NMR,13 C NMR and HR-ESI-MS.
Eleven novel quaternary 3-aminomethyl oxindole compounds,in yield of 68% ~ 98%,were efficiently synthesized by Mannich reaction of 3-substituted oxindoles with imine precursors,using TBAB as the phase transfer catalyst. The structures were characterized by1 H NMR,13 C NMR and HR-ESI-MS.
引文
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[3]Dounay A B,Overman L E.The asymmetric intramolecular Heck reaction in natural product total synthesis[J].Chem Rev,2003,103:2945-2964.
[4]Lin H,Danishefsky S J.Gelsemine:A thought-provoking target for total synthesis[J].Angew Chem Int Ed,2003,42:36-51.
[5]黄璇,郭丰敏,刘雄伟,等.新型3-季碳羟甲基(或3-季碳甲基)氧化吲哚的合成[J].合成化学,2014,22(4):499-503.
[6]Ishimaru T,Shibata N,Nagai J,et al.Lewis acidcatalyzed enantioselective hydroxylation reactions of oxindoles andβ-keto esters using DBFOX ligand[J].J Am Chem Soc,2006,128:16488-16489.
[7]Tomita D,Yamatsugu K,Kanai M,et al.Enantioselective synthesis of SM-130686 based on the development of asymmetric Cu(I)F catalysis to access 2-oxindoles containing a tetrasubstituted carbon[J].J Am Chem Soc,2009,131:6946-6948.
[8]Trost B M,Zhang Y.Mo-catalyzed regio-,diastereo-and enantioselective allylic alkylation of 3-aryloxindoles[J].J Am Chem Soc,2007,129:14548-14549.
[9]Hills I D,Fu G C.Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter[J].Angew Chem Int Ed,2003,42:3921-3924.
[10]Shaw S A,Aleman P,Christy J,et al.Enantioselective TADMAP-catalyzed carboxyl migration reactions for the synthesis of stereogenic quaternary carbon[J].J Am Chem Soc,2006,128:925-934
[11]Zhou F,Ding M,Zhou J.Organocatalytic asymmetric a-amination of unprotected 3-aryl and 3-aliphatic substituted oxindoles using di-tert-butyl azodicarboxylate[J].Adv Synth Catal,2011,353:2945-2952.
[12]Kang Q,Zhao Z A,You S L.Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid[J].J Am Chem Soc,2007,129:1484-1485.
[13]Tian X,Jiang K,Peng J,et al.Organocatalytic stereoselective Mannichreaction of 3-substituted oxindoles[J].Organic Letter 2008,10:3583-3586.