Sulfamidation of 2-arylaldehydes and ketones with chloramine-T

被引:31
作者
Baumann, Thomas [1 ]
Baechle, Michael [1 ]
Braese, Stefan [1 ]
机构
[1] Univ Karlsruhe, Inst Organ Chem, TH, D-76131 Karlsruhe, Germany
关键词
D O I
10.1021/ol061410g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either alpha-sulfamidation in the case of aromatic aldehydes and acetone derivatives or direct sulfamidation at the carbonyl functionality of aliphatic aldehydes has been observed. Applying microwave conditions, good to excellent yields under significantly reduced reaction times could be obtained, thus providing a facile access to alpha, alpha-disubstituted amino acids.
引用
收藏
页码:3797 / 3800
页数:4
相关论文
共 44 条
[1]   Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source [J].
Ando, T ;
Minakata, S ;
Ryu, I ;
Komatsu, M .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :309-312
[2]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[3]   Chiral C2-symmetric bisferrocenyldiamines as ligands for transition metal catalyzed asymmetric cyclopropanation and aziridination [J].
Cho, DJ ;
Jeon, SJ ;
Kim, HS ;
Cho, CS ;
Shim, SC ;
Kim, TJ .
TETRAHEDRON-ASYMMETRY, 1999, 10 (19) :3833-3848
[4]   SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].
DALCANALE, E ;
MONTANARI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569
[5]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[6]   BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS [J].
EVANS, DA ;
FAUL, MM ;
BILODEAU, MT ;
ANDERSON, BA ;
BARNES, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5328-5329
[7]  
Fokin VV, 2001, ANGEW CHEM INT EDIT, V40, P3455, DOI 10.1002/1521-3773(20010917)40:18<3455::AID-ANIE3455>3.0.CO
[8]  
2-I
[9]  
GEETHANJALI A, 2005, SYNLETT, V18, P2857
[10]   Enantioselective aziridination using copper complexes of biaryl Schiff bases [J].
Gillespie, KM ;
Sanders, CJ ;
O'Shaughnessy, P ;
Westmoreland, I ;
Thickitt, CP ;
Scott, P .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3450-3458