Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones

被引:66
作者
Gu, Zhenhua [1 ]
Herrmann, Aaron T. [1 ]
Zakarian, Armen [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
基金
美国国家卫生研究院;
关键词
haloalkylation; homogeneous catalysis; radicals; tautomerism; titanium enolates; VALENCE TAUTOMERISM; RUCL(CP-ASTERISK)(PPH3)(2); AUXILIARY;
D O I
10.1002/anie.201101364
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Waste not, want not: A mechanistic study of the ruthenium-catalyzed haloalkylation of titanium enolates led to the development of a process that is catalytic in both metals: titanium and ruthenium (see scheme; Bn=benzyl, PMP=1,2,2,6,6-pentamethylpiperidine). Catalytic turnover was observed in the formation of the titanium enolates from N-acyl oxazolidinones, and insight was gained into the inhibitory effect of the amine base. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7136 / 7139
页数:4
相关论文
共 24 条
[1]  
Amatov T., 2011, ANGEW CHEM, V123, P4636
[2]   Perhaloalkylation of Metal Enolates-Unconventional and Versatile [J].
Amatov, Tynchtyk ;
Jahn, Ullrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (20) :4542-4544
[3]   Asymmetric synthesis of dideazafolate antitumor agents via amidomethylation of nonracemic oxazolidinone imidates. Synthesis of LY309887, a cytotoxic dideazafolate analog related to lometrexol [J].
Barnett, CJ ;
Wilson, TM ;
Evans, DA ;
Somers, TC .
TETRAHEDRON LETTERS, 1997, 38 (05) :735-738
[4]   Valence Tautomerism in Titanium Enolates: Catalytic Radical Haloalkylation and Application in the Total Synthesis of Neodysidenin [J].
Beaumont, Stephane ;
Ilardi, Elizabeth A. ;
Monroe, Lucas R. ;
Zakarian, Armen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1482-+
[5]   2-(N-METHYLANILINO)-2-PHENYLSULFANYLACETONITRILE, A REAGENT TESTED FOR ELECTROPHILIC, NUCLEOPHILIC AND RADICAL REACTIONS [J].
CHEN, CC ;
CHEN, ST ;
CHUANG, TH ;
FANG, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (16) :2217-2221
[6]   Stepwise substitution of N,N-di-isopropylcarbamato groups of Ti(O2CNiPr2)4 by triphenylsilanol leading from eight- to six- and four-co-ordinated titanium(IV) [J].
Dell'Amico, DB ;
Calderazzo, F ;
Ianelli, S ;
Labella, L ;
Marchetti, F ;
Pelizzi, G .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (23) :4339-4342
[7]   Valence tautomerism: New challenges for electroactive ligands [J].
Evangelio, E ;
Ruiz-Molina, D .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (15) :2957-2971
[8]   TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC IONOMYCIN [J].
EVANS, DA ;
DOW, RL ;
SHIH, TL ;
TAKACS, JM ;
ZAHLER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5290-5313
[9]   NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].
EVANS, DA ;
URPI, F ;
SOMERS, TC ;
CLARK, JS ;
BILODEAU, MT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216
[10]   The persistent radical effect: A principle for selective radical reactions and living radical polymerizations [J].
Fischer, H .
CHEMICAL REVIEWS, 2001, 101 (12) :3581-3610