Reagent-controlled regioselective [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydroxylamine and its synthetic application

被引：5

作者：

Takeda, Norihiko ^{[1
]}

Miyata, Okiko ^{[1
]}

Kitamura, Maria ^{[1
]}

Kagehira, Shunsuke ^{[1
]}

Naito, Takeaki ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan

来源：

SYNLETT | 2006年 / 20期

关键词：

benzofuran; enehydroxylamine; 3,3]-sigmatropic rearrangement; lunarine; galanthamine;

D O I：

10.1055/s-2006-958431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective [3,3]-sigmatropic rearrangement provides a novel method for the construction of hexahydrodibenzofuran with a quaternary carbon in the ring juncture. Upon treatment with TFAA. oxime ethers carrying an electron-withdrawing group smoothly underwent regioselective rearrangement to give the hexahydrodibenzofuran with a quaternary carbon. On the other hand, the reaction of oxime ethers with TFAT-DMAP gave tetrahydrodibenzofurans carrying a substituent at the 4-position. The hexahydrodibenzofuran with a quaternary carbon was effectively converted into a key intermediate for lunarine synthesis.

引用

页码：3415 / 3418

页数：4

共 50 条

[41] POTENTIAL SYNTHETIC UTILITY OF [3,3]-SIGMATROPIC REARRANGEMENT OF S-ALLYL DITHIOCARBAMATES NEW ROUTES TO ALPHA, BETA-UNSATURATED ALDEHYDES
NAKAI, T
SHIONO, H
OKAWARA, M
TETRAHEDRON LETTERS, 1974, (41) : 3625 - 3628
[42] A new synthetic route to nucleosides: Dissymmetric construction of a cyclopentene system by double [3,3]-sigmatropic rearrangement and double ring-closing metathesis
Fang, Z
Hong, JH
ORGANIC LETTERS, 2004, 6 (06) : 993 - 995
[43] Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: Short syntheses of stemofuran A and eupomatenoid 6
Miyata, O
Takeda, N
Naito, T
ORGANIC LETTERS, 2004, 6 (11) : 1761 - 1763
[44] Gold-Catalyzed Addition of N-Hydroxy Heterocycles to Alkynes and Subsequent 3,3-Sigmatropic Rearrangement
Kumar, Manish
Scobie, Martin
Mashuta, Mark S.
Hammond, Gerald B.
Xu, Bo
ORGANIC LETTERS, 2013, 15 (04) : 724 - 727
[45] n-Butyllithium-Induced Tandem [3,3]-Sigmatropic Rearrangement and Carbonyl Olefination of Allyl-1,1-dichlorovinyl Ethers
Christopher, Aaron
Brandes, Dahniel
Kelly, Stephen
Minehan, Thomas G.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17487 - 17495
[46] Regioselective Synthesis of 2-(Trifluoromethyl)-3-ethoxycarbonyl-4-(2-oxo-2-arylethyl)-4H-chromene Derivatives by [3,3] Sigmatropic Rearrangement
Kuchukulla, Ratnakar Reddy
Desagoni, Madhu
Narra, Srikanth Reddy
Goutham, Santhosh Kumar
Banda, Narsaiah
CHEMISTRYSELECT, 2017, 2 (35): : 11545 - 11547
[47] Palladium-catalyzed [3,3] sigmatropic rearrangement of (allyloxy)iminodiazaphospholidines: Allylic transposition of C-O and C-N functionality
Lee, EE
Batey, RA
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (14) : 1865 - 1868
[48] [3,3]SIGMATROPIC REARRANGEMENT OF AN N-BENZOYL-3,6-DIHYDRO-1,2-OXAZINE DERIVED FROM ERGOSTERYL ACETATE AND NITROSOCARBONYLBENZENE
KIRBY, GW
MACKINNON, JWM
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (01) : 23 - 24
[49] Sequential [3,3]-Sigmatropic Rearrangement/Nucleophilic Arylation of N-(Benzoyloxy)enamides towards the Preparation of Cyclic -Aryl--amino Alcohols
Sato, Shohei
Takeda, Norihiko
Ueda, Masafumi
Miyata, Okiko
SYNTHESIS-STUTTGART, 2016, 48 (06): : 882 - 892
[50] Polyhetero[3,3]-sigmatropic rearrangement of O(S)-methyl-S(O)allyl-N-(9-acridinyl)iminothiocarbonates
Kristian, P
Hocova, S
Bernat, J
Busova, T
Chomca, I
HETEROCYCLES, 1998, 47 (01) : 505 - 508

← 1 2 3 4 5 →