Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation

被引：74

作者：

Liu, Lei ^{[1
]}

Floreancig, Paul E. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 14期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

C-H ACTIVATION; TRIISOPROPYLSILYL ENOL ETHERS; CARBON BOND FORMATION; CHIRAL ENAMIDES; ELECTROSTATIC STABILIZATION; OXOCARBENIUM IONS; LEWIS-ACID; AMIDES; REACTIVITY; FUNCTIONALIZATION;

D O I：

10.1021/ol901188q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

引用

页码：3152 / 3155

页数：4

共 50 条

[31] SMI2-MEDIATED CYCLIZATION OF VINYL RADICALS
CAPELLA, L
MONTEVECCHI, PC
TETRAHEDRON LETTERS, 1994, 35 (45) : 8445 - 8448
[32] Electroorganic reactions. Part 57. DDQ mediated anodic oxidation of 2-methyl- and 2-benzylnaphthalenes
Utley, J.H.P.
Rozenberg, G.G.
Utley, J.H.P. (j.utley@gmul.ac.uk), 1600, Kluwer Academic Publishers (33):
[33] Electroorganic reactions. Part 57. DDQ mediated anodic oxidation of 2-methyl- and 2-benzylnaphthalenes
Utley, JHP
Rozenberg, GG
JOURNAL OF APPLIED ELECTROCHEMISTRY, 2003, 33 (06) : 525 - 532
[34] Electroorganic reactions. Part 57.† DDQ mediated anodic oxidation of 2-methyl- and 2-benzylnaphthalenes
J.H.P. Utley
G.G. Rozenberg
Journal of Applied Electrochemistry, 2003, 33 : 525 - 532
[35] DDQ-mediated oxidation of 4,6-O-methoxybenzylidene-protected saccharides in the presence of various nucleophiles: Formation of 4-OH, 6-Cl, and 6-Br derivatives
Zhang, ZY
Magnusson, G
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07): : 2394 - 2400
[36] Mild synthesis of mercaptonitriles from vinyl nitriles and their cyclization reactions
Caspari, Philip
Nuesch, Frank A.
Neels, Antonia
Opris, Dorina M.
RSC ADVANCES, 2016, 6 (100): : 98059 - 98065
[37] Tin-Mediated Radical Cyclization Reactions
Malik, Saima
Lavekar, Aditya G.
Banik, Bimal Krishna
CURRENT ORGANIC CHEMISTRY, 2021, 25 (22) : 2708 - 2739
[38] Photoinduced Synthesis of Bis-Sulfonyl γ-Arylated Ketones via DMAP/DDQ-Mediated Stereogenic Conjugated Addition of α-Sulfonyl Chalcones with Benzylic Sulfones
Hsueh, Nai-Chen
Chang, Meng-Yang
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (04) : 544 - 554
[39] Diastereoselective, titanium-mediated cyclization of ω-vinyl tethered imides
Santra, S
Masalov, N
Epstein, OL
Cha, JK
ORGANIC LETTERS, 2005, 7 (26) : 5901 - 5904
[40] SILYLATION-MEDIATED OXIDATION OF 4-AZA-3-KETOSTEROIDS WITH DDQ PROCEEDS VIA DDQ-SUBSTRATE ADDUCTS
BHATTACHARYA, A
DIMICHELE, LM
DOLLING, UH
DOUGLAS, AW
GRABOWSKI, EJJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) : 3318 - 3319

← 1 2 3 4 5 →