Instantaneous Deprotection of Tosylamides and Esters with SmI2/Amine/Water

被引:156
作者
Ankner, Tobias [1 ]
Hilmersson, Goeran [1 ]
机构
[1] Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden
关键词
ASYMMETRIC ADDITION; N-TOSYLARYLIMINES; ALKYL-HALIDES; REDUCTION; CLEAVAGE; AMINES; SMI2/H2O/AMINE; MILD; ARENESULFONAMIDES; ARYLATION;
D O I
10.1021/ol802243d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sml(2)amine/water mediates instantaneous cleavage of tosyl amides and tosyl esters. Highly hindered, sensitive and functionalized substrates were successfully deprotected in near quantitative yield.
引用
收藏
页码:503 / 506
页数:4
相关论文
共 38 条
[1]   Deprotection of sulfonyl aziridines [J].
Alonso, DA ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9455-9461
[2]   Instantaneous SmI2/H2O/amine mediated reduction of nitroalkanes and α,β-unsaturated nitroalkenes [J].
Ankner, Tobias ;
Hilmersson, Goran .
TETRAHEDRON LETTERS, 2007, 48 (32) :5707-5710
[3]   THE REGIOSELECTIVE CLEAVAGE OF ARYL TOSYLATES BY ELECTROCHEMICAL REDUCTION [J].
CIVITELLO, ER ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :834-840
[4]   Mild electrochemical deprotection of N-phenylsulfonyl N-substituted amines derived from (R)-phenylglycinol [J].
Coeffard, Vincent ;
Thobie-Gautier, Christine ;
Beaudet, Isabelle ;
Le Grognec, Erwan ;
Quintard, Jean-Paul .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (02) :383-391
[5]   Estimating the limiting reducing power of SmI2/H2O/amine and YbI2/H2O/amine by efficient reduction of unsaturated hydrocarbons [J].
Dahlén, A ;
Nilsson, Å ;
Hilmersson, G .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1576-1580
[6]   Mechanistic study of the Sml2/H2O/amine-mediated reduction of alkyl halides:: Amine base strength (pKBH+) dependent rate [J].
Dahlén, A ;
Hilmersson, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8340-8347
[7]   Rapid SmI2-mediated reductions of alkyl halides and electrochemical properties of SmI2/H2O/amine [J].
Dahlén, A ;
Hilmersson, G ;
Knettle, BW ;
Flowers, RA .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4870-4875
[8]   Instantaneous SmI2/H2O/amine-mediated reductions in THF [J].
Dahlén, A ;
Hilmersson, G .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (05) :1123-1128
[9]   Diastereoselective intramolecular SmI2-H2O-amine mediated couplings [J].
Dahlén, A ;
Petersson, A ;
Hilmersson, G .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (14) :2423-2426
[10]   Selective reduction of carbon-carbon double and triple bonds in conjugated olefins mediated by SMI2/H2O/amine in THF [J].
Dahlén, A ;
Hilmersson, G .
TETRAHEDRON LETTERS, 2003, 44 (13) :2661-2664