Alkylative amination of aldehydes via carbon-carbon bond formation based on radical addition to carbon-nitrogen double bond

被引：34

作者：

Miyabe, H ^{[1
]}

Yamakawa, K ^{[1
]}

Yoshioka, N ^{[1
]}

Naito, T ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1999年 / 55卷 / 37期

关键词：

radical addition; oxime ether; atom-transfer; one-pot; amination;

D O I：

10.1016/S0040-4020(99)00643-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylative amination of aldehydes was achieved via a carbon-carbon bond formation by the intermolecular alkyl radical addition to the carbon-nitrogen double bond of oxime ethers generated in situ from aldehydes and benzyloxyamine. Alkyl radical addition to oxime ethers via a route involving the iodine atom-transfer process was found to be largely dependent on the reaction temperature and eliminated the tedious workup to remove excess tin-residues From the reaction mixture. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11209 / 11218

页数：10

共 30 条

[1]

Akiyama T, 1998, SYNLETT, P273

[2]

Arend M, 1997, SYNLETT, P974

[3] Synthesis of novel nucleic acid mimics via the stereoselective intermolecular radical coupling of 3'-iodo nucleosides and formaldoximes [J].

Bhat, B ;

Swayze, EE ;

Wheeler, P ;

Dimock, S ;

Perbost, M ;

Sanghvi, YS .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8186-8199

[4] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[5] Synthesis of trehazolin from D-glucose [J].

Boiron, A ;

Zillig, P ;

Faber, D ;

Giese, B .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :5877-5882

[6] Preparation of alpha-(2,2-diphenylhydrazino)- and alpha-(benzyloxyamino)-lactones by radical cyclization: Use of glyoxylic acid diphenylhydrazone and glyoxylic acid O-benzyloxime [J].

Clive, DLJ ;

Zhang, J .

CHEMICAL COMMUNICATIONS, 1997, (06) :549-550

[7]

Giese B., 2004, Organic Reactions, P301, DOI [10.1002/0471264180.or048.02, DOI 10.1002/0471264180.OR048.02]

[8] Radical cyclizations of acylgermane oxime ethers and hydrazones: Direct routes to cyclic hydrazones and oximes [J].

Iserloh, U ;

Curran, DP .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14) :4711-4716

[9] Total synthesis of ent-lycoricidine via a thiyl radical addition-cyclization sequence [J].

Keck, GE ;

Wager, TT .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8366-8367

[10] Novel radical reaction of phenylsulfonyl oxime ethers. A free radical acylation approach [J].

Kim, S ;

Lee, IY ;

Yoon, JY ;

Oh, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5138-5139

← 1 2 3 →