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
收藏
页码：1451 / 1453
页数：3
相关论文
共 59 条
[31]  
KRESZE G, 1987, ORG SYNTH, V65, P159
[32]   AMINATION OF OLEFINIC COMPOUNDS WITH BIS(2,2,2-TRICHLOROETHYL) AZODICARBOXYLATE [J].
LEBLANC, Y ;
ZAMBONI, R ;
BERNSTEIN, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1971-1972
[33]   1ST D0 METALLOOXAZIRIDINES - AMINATION OF OLEFINS [J].
LIEBESKIND, LS ;
SHARPLESS, KB ;
WILSON, RD ;
IBERS, JA .
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 [J].
Lin, YS ;
El Ali, B ;
Alper, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7719-7720
[35]   THE STABILITY OF AQUEOUS SOLUTIONS OF HYDROXYLAMINE-O-SULPHONIC ACID [J].
MATSUGUMA, HJ ;
AUDRIETH, LF .
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 [J].
MATTINGLY, PG ;
MILLER, MJ .
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 [J].
Pohlki, F ;
Doye, S .
CHEMICAL SOCIETY REVIEWS, 2003, 32 (02) :104-114
[40]  
RICCI A, 2000, REV MODERN AMINATION
123456