Gold-catalyzed efficient preparation of linear α-haloenones from propargylic acetates

被引：66
作者：
Yu, Meng [1 ]
Zhang, Guozhu [1 ]
Zhang, Liming [1 ]
机构：
[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA
来源：
TETRAHEDRON | 2009年 / 65卷 / 09期
关键词：
ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; HIGHLY EFFICIENT; GOLD(I)-CATALYZED FORMATION; TANDEM; CYCLOISOMERIZATION; KETONES; REARRANGEMENT; ALKYNES; ACCESS; ENYNES;
D O I：
10.1016/j.tet.2008.11.107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Versatile linear alpha-iodo- and alpha-bromoenones are prepared efficiently from readily accessible propargylic acetates using 2 mol % of Au(PPh3)NTf2. This reaction is easy to execute and has broad substrate scope. Good to excellent Z-selectivities are observed in the cases of propargylic acetates derived from aliphatic aldehydes. (C) 2008 Published by Elsevier Ltd.
引用
收藏
页码：1846 / 1855
页数：10
相关论文
共 61 条
[21]   Gold(I)-catalyzed stereoselective olefin cyclopropanation [J].
Johansson, MJ ;
Gorin, DJ ;
Staben, ST ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18002-18003
[22]   DIRECT ALPHA-IODINATION OF CYCLOALKENONES [J].
JOHNSON, CR ;
ADAMS, JP ;
BRAUN, MP ;
SENANAYAKE, CBW ;
WOVKULICH, PM ;
USKOKOVIC, MR .
TETRAHEDRON LETTERS, 1992, 33 (07) :917-918
[23]   A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE® and hydrohalic acid (HBr, HCl) [J].
Kim, KM ;
Park, IH .
SYNTHESIS-STUTTGART, 2004, (16) :2641-2644
[24]   Catalyzed tandem reaction of 3-silyloxy-1,5-enynes consisting of cyclization and pinacol rearrangement [J].
Kirsch, Stefan F. ;
Binder, Joerg T. ;
Crone, Benedikt ;
Duschek, Alexander ;
Haug, Timm T. ;
Liebert, Clemence ;
Menz, Helge .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) :2310-2313
[25]   A convenient protocol for the α-iodination of α,β-unsaturated carbonyl compounds with I2 in an aqueous medium [J].
Krafft, ME ;
Cran, JW .
SYNLETT, 2005, (08) :1263-1266
[26]   Gold-catalyzed organic transformations [J].
Li, Zigang ;
Brouwer, Chad ;
He, Chuan .
CHEMICAL REVIEWS, 2008, 108 (08) :3239-3265
[27]   Complex α-pyrones synthesized by a gold-catalyzed coupling reaction [J].
Luo, Tuoping ;
Schreiber, Stuart L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (43) :8250-8253
[28]   Gold-catalyzed cyclization of enynes [J].
Ma, SM ;
Yu, SC ;
Gu, ZH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (02) :200-203
[29]   Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes [J].
Mamane, V ;
Gress, T ;
Krause, H ;
Fürstner, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8654-8655
[30]   [(NHC)AuI]-catalyzed formation of conjugated enones and enals:: An experimental and computational study [J].
Marion, Nicolas ;
Carlqvist, Peter ;
Gealageas, Ronan ;
de Fremont, Pierre ;
Maseras, Feliu ;
Nolan, Steven P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (22) :6437-6451
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