Carbon-carbon bond formation via intermolecular carbon radical addition to aldoxime ethers

被引：69

作者：

Miyabe, H ^{[1
]}

Shibata, R ^{[1
]}

Ushiro, C ^{[1
]}

Naito, T ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe, Hyogo 658, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)10663-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of intermolecular carbon radical addition to unactivated aldoxime ethers in the presence of BF3 . OEt2 has provided a new efficient carbon-carbon bond-forming method for the synthesis of a variety of amines. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：631 / 634

页数：4

相关论文

共 30 条

[1]

[Anonymous], [No title captured]

[2] 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

[3] INTRAMOLECULAR REDUCTIVE COUPLING OF CARBONYL-TETHERED OXIME ETHERS PROMOTED BY SAMARIUM DIIODIDE - A POWERFUL METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF AMINOCYCLOPENTITOLS [J].

CHIARA, JL ;

MARCOCONTELLES, J ;

KHIAR, N ;

GALLEGO, P ;

DESTABEL, C ;

BERNABE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6010-6011

[4]

Clive D. L. J., 1997, J CHEM SOC CHEM COMM, P549

[5] A NEW SYNTHETIC ROUTE TO PROSTAGLANDINS [J].

COREY, EJ ;

NIIMURA, K ;

KONISHI, Y ;

HASHIMOTO, S ;

HAMADA, Y .

TETRAHEDRON LETTERS, 1986, 27 (20) :2199-2202

[6]

DENMARK SE, 1997, CHEM COMMUN, P999

[7] 1,2-NUCLEOPHILIC ADDITIONS OF ORGANOLITHIUM REAGENTS TO CHIRAL OXIME ETHERS [J].

DIETER, RK ;

DATAR, R .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1993, 71 (06) :814-823

[8] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[9]

FIAUD JC, 1971, TETRAHEDRON LETT, P1019

[10] The asymmetric synthesis of allylglycine and other unnatural alpha-amino acids via zinc-mediated allylation of oximes in aqueous media [J].

Hanessian, S ;

Yang, RY .

TETRAHEDRON LETTERS, 1996, 37 (30) :5273-5276