Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5+2] annulation

被引：50

作者：

Cui, Li ^{[1
]}

Ye, Longwu ^{[1
]}

Zhang, Liming ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 19期

关键词：

PONNDORF-VERLEY REDUCTION; ASYMMETRIC REDUCTION; RING-CLOSURE; AU CATALYSIS; MIGRATION; ANALOGS; ALLENES; OLEFINS; KETONES; ALKYNES;

D O I：

10.1039/c001314e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A surprisingly efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation is developed. This reaction involves a key gold catalysis and shows generally high regioselectivities and good to excellent diastereoselectivities.

引用

页码：3351 / 3353

页数：3

共 32 条

[1] SELECTIVITY IN AN ASYMMETRIC NITROGEN INSERTION PROCESS
AUBE, J
BURGETT, PM
WANG, Y
[J]. TETRAHEDRON LETTERS, 1988, 29 (02) : 151 - 154
[2] A Gold-Catalyzed Cascade Reaction Involving an Unusual Intramolecular Redox Process
Barluenga, Jose
Fernandez, Amadeo
Rodriguez, Felix
Fananas, Francisco J.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (33) : 8121 - 8123
[3] REARRANGEMENT OF AN ORTHO-SUBSTITUTED PHENYL RADICAL BY 1,7-HYDROGEN ATOM MIGRATION
BECKWITH, ALJ
BOATE, DR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (12) : 797 - 798
[4] Gold-Catalyzed 1,3-Addition of a Sp3-Hybridized C-H Bond to Alkenylcarbenoid Intermediate
Bhunia, Sabyasachi
Liu, Rai-Shung
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) : 16488 - +
[5] Application of a double Mannich reaction using bis(aminol) ethers in the synthesis of AE ring analogues of methyl lycaconitine
Brocke, C
Brimble, MA
Lin, DSH
McLeod, MD
[J]. SYNLETT, 2004, (13) : 2359 - 2363
[6] New hindered isomers of 3-dehydroretinal (vitamin A(2))
Chen, RL
Liu, RSH
[J]. TETRAHEDRON, 1996, 52 (23) : 7809 - 7816
[7] Total synthesis of (+)-lentiginosine via a key Au catalysis
Cui Li
Zhang LiMing
[J]. SCIENCE CHINA-CHEMISTRY, 2010, 53 (01) : 113 - 118
[8] Homogeneous gold-catalyzed efficient oxidative dimerization of propargylic acetates
Cui, Li
Zhang, Guozhu
Zhang, Liming
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (14) : 3884 - 3887
[9] A Two-Step, Formal [4+2] Approach toward Piperidin-4-ones via Au Catalysis
Cui, Li
Peng, Yu
Zhang, Liming
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) : 8394 - +
[10] Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[b]azepin-4-ones from Tertiary N-(But-3-ynyl)anilines
Cui, Li
Zhang, Guozhu
Peng, Yu
Zhang, Liming
[J]. ORGANIC LETTERS, 2009, 11 (06) : 1225 - 1228

← 1 2 3 4 →