Gold(I)-catalyzed hydroaminative cyclization leading to 2,5-dihydroisoxazole

被引:43
作者
Yeom, Hyun-Suk [1 ]
Lee, Eun-Sun [1 ]
Shin, Seunghoon [1 ]
机构
[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea
关键词
2,5-dihydroisoxazoles; heterocycles; cyclizations gold catalysis; carbenoids;
D O I
10.1055/s-2007-985571
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Gold(I)-catalyzed intramolecular hydroamination of O-propargyl-N-Boc-hydroxylamine is reported. The present method provides a novel, catalytic, and mild approach to 2,5-dihydroisoxazole derivatives. In addition, a mechanism of N-O cleavage as a side reaction as well as desired cyclization is proposed.
引用
收藏
页码:2292 / 2294
页数:3
相关论文
共 50 条
[21]   Gold catalysis [J].
Hashmi, A. Stephen K. ;
Hutchings, Graham J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) :7896-7936
[22]   Isoindoles and dihydroisoquinolines by gold-catalyzed intramolecular hydroamination of alkynes [J].
Kadzimirsz, D ;
Hildebrandt, D ;
Merz, K ;
Dyker, G .
CHEMICAL COMMUNICATIONS, 2006, (06) :661-662
[23]   Gold(I)-catalyzed intramolecular hydroamination of alkyne with trichloroacetimidates [J].
Kang, Ji-Eun ;
Kim, Hak-Beom ;
Lee, Jin-Woo ;
Shin, Seunghoon .
ORGANIC LETTERS, 2006, 8 (16) :3537-3540
[24]   An approach to 2,3-dihydropyrroles and β-iodopyrroles based on 5-endo-dig cyclisations [J].
Knight, DW ;
Redfern, AL ;
Gilmore, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (05) :622-628
[25]   A transient N-O-linked Pauson-Khand strategy for the synthesis of the deschloro carbocyclic core of the palau'amines and styloguanidines [J].
Koenig, SG ;
Miller, SM ;
Leonard, KA ;
Löwe, RS ;
Chen, BC ;
Austin, DJ .
ORGANIC LETTERS, 2003, 5 (13) :2203-2206
[26]   THE ISOXAZOLINE ROUTE TO THE MOLECULES OF NATURE [J].
KOZIKOWSKI, AP .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (12) :410-416
[27]   Gold(I)-catalyzed enantioselective intramolecular hydroamination of allenes [J].
LaLonde, Rebecca L. ;
Sherry, Benjamin D. ;
Kang, Eun Joo ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (09) :2452-+
[28]  
LI G, 2007, IN PRESS ANGEW CHEM, V46
[29]   Phosphine gold(I)-catalyzed hydroamination of alkenes under thermal and microwave-assisted conditions [J].
Liu, Xin-Yuan ;
Li, Cheng-Hui ;
Che, Chi-Ming .
ORGANIC LETTERS, 2006, 8 (13) :2707-2710
[30]   Au(I)-catalyzed highly efficient intermolecular hydroamination of alkynes [J].
Mizushima, E ;
Hayashi, T ;
Tanaka, M .
ORGANIC LETTERS, 2003, 5 (18) :3349-3352