Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy,N-oxyenamines

被引：23

作者：

Kokuev, Aleksandr O. ^{[1
,2
]}

Antonova, Yulia A. ^{[1
,3
]}

Dorokhov, Valentin S. ^{[1
,2
]}

Golovanov, Ivan S. ^{[1
]}

Nelyubina, Yulia V. ^{[4
]}

Tabolin, Andrey A. ^{[1
]}

Sukhorukov, Alexey Yu. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia

[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Miusskaya Sq 9, Moscow 125047, Russia

[3] Moscow MV Lomonosov State Univ, Dept Chem, Leninskie Gory 1, Moscow 119991, Russia

[4] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilov Str 28, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 18期

基金：

俄罗斯科学基金会;

关键词：

COPE REARRANGEMENT; ALPHA-OXYGENATION; INDOLE SYNTHESIS; N-OXIDES; ALDEHYDES; CYCLOADDITION; HYDROLYSIS; ION;

D O I：

10.1021/acs.joc.8b01652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acylation of nitronates affords alpha-acyloxyoxime derivatives via an umpolung functionalization of the alpha-position. This transformation involves generation of hitherto unknown N-acyloxy,N-oxyenamines and their fast [3,3]-sigmatropic rearrangement driven by the cleavage of the weak N-O bond. The reaction has a broad scope, and it is regioselective in the case of nitronates possessing nonsymmetrically substituted alpha-positions. Application to the formal total synthesis of clausenamide and cis-clausenamide is presented.

引用

页码：11057 / 11066

页数：10

共 50 条

[31] S-Allyl Thiocarbamates from Allylic Alcohols by in situ [3,3]-Sigmatropic Rearrangement of a Thiocarbonyldiimidazole Adduct
Mingat, Gaelle
Clayden, Jonathan
SYNTHESIS-STUTTGART, 2012, 44 (17): : 2723 - 2734
[32] A highly diastereoselective [2,3]-sigmatropic N,O rearrangement
Bull, SD
Davies, SG
Jones, S
Ouzman, JVA
Price, AJ
Watkin, DJ
CHEMICAL COMMUNICATIONS, 1999, (20) : 2079 - 2080
[33] 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
[34] N-(HETEROCYCLIC)SULPHENAMIDES BY [2,3] SIGMATROPIC REARRANGEMENT OF SULFILIMINES
ATKINSON, RS
AWAD, SB
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (15) : 651 - 652
[35] 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
[36] [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
[37] The [2,3] sigmatropic rearrangement of N-benzyl-O-allylhydroxylamines
Davies, SG
Fox, JF
Jones, S
Price, AJ
Sanz, MA
Sellers, TGR
Smith, AD
Teixeira, FC
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (15): : 1757 - 1765
[38] AN ADVANTAGEOUS SYNTHESIS OF S-(2-PROPENYL) N-ACYLMONOTHIOCARBAMATES BY [3,3]-SIGMATROPIC REARRANGEMENT OF O-(2-PROPENYL) N-ACYLMONOTHIOCARBAMATES
KUTSCHY, P
DZURILLA, M
KOSCIK, D
KRISTIAN, P
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1987, 52 (07) : 1764 - 1772
[39] 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
[40] 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 →