Copper-catalyzed allylic hydroxyamination and amination of alkenes with Boc-hydroxylamine

被引：26

作者：

Kalita, B ^{[1
]}

Nicholas, KM ^{[1
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 09期

基金：

美国国家科学基金会;

关键词：

allylic amination; hydroxyamination; copper-catalyzed;

D O I：

10.1016/j.tetlet.2005.01.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Olefins react regioselectively with Boc-NHOH in the presence of Cu(I,II) salts to produce allyl-N(OH)(Boc) derivatives, apparently via the intermediacy of Boc-N=O; yields and rates are dramatically improved by the addition of H2O2. The corresponding allylamine derivatives, allyl-NH(Boc), are formed selectively from Boc-NHOH/olefin with CuBr/P(OEt)(3). (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1451 / 1453

页数：3

共 59 条

[31] KRESZE G, 1987, ORG SYNTH, V65, P159
[32] AMINATION OF OLEFINIC COMPOUNDS WITH BIS(2,2,2-TRICHLOROETHYL) AZODICARBOXYLATE
LEBLANC, Y
ZAMBONI, R
BERNSTEIN, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1971 - 1972
[33] 1ST D0 METALLOOXAZIRIDINES - AMINATION OF OLEFINS
LIEBESKIND, LS
SHARPLESS, KB
WILSON, RD
IBERS, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (22) : 7061 - 7063
[34] A novel one-pot reaction: Zwitterionic rhodium complex-catalyzed hydroaminovinylation of vinyl sulfones and a vinylphosphonate
Lin, YS
El Ali, B
Alper, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) : 7719 - 7720
[35] THE STABILITY OF AQUEOUS SOLUTIONS OF HYDROXYLAMINE-O-SULPHONIC ACID
MATSUGUMA, HJ
AUDRIETH, LF
[J]. JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1959, 12 (1-2): : 186 - 192
[36] TITANIUM TRICHLORIDE REDUCTION OF SUBSTITUTED N-HYDROXY-2-AZETIDINONES AND OTHER HYDROXAMIC ACIDS
MATTINGLY, PG
MILLER, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (03) : 410 - 415
[37] Muller P, 1997, ADV CAT PROCESS, V2, P113
[38] Muller T. E., 1998, TRANSITION METALS OR, V2, P316
[39] The catalytic hydroamination of alkynes
Pohlki, F
Doye, S
[J]. CHEMICAL SOCIETY REVIEWS, 2003, 32 (02) : 104 - 114
[40] RICCI A, 2000, REV MODERN AMINATION

← 1 2 3 4 5 6 →