Cobalt-catalyzed hydrohydrazination of dienes and enynes:: Access to allylic and propargylic hydrazides

被引：84

作者：

Waser, J ^{[1
]}

González-Gómez, JC ^{[1
]}

Nambu, H ^{[1
]}

Huber, P ^{[1
]}

Carreíra, EM ^{[1
]}

机构：

[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 19期

关键词：

D O I：

10.1021/ol0517473

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cobalt-catalyzed hydrohydrazination reaction of dienes and enynes is presented. Allylic and propargylic hydrazines were obtained in synthetically useful yields (allylic amines, 60-90%; propargylic arnines, 47-83%) and good chemo- and regioselectivity.

引用

页码：4249 / 4252

页数：4

共 42 条

[1] STANNYLMETALLATION OF CONJUGATED ENYNES [J].

AKSELA, R ;

OEHLSCHLAGER, AC .

TETRAHEDRON, 1991, 47 (07) :1163-1176

[2] 2,3-DIAZABICYCLO[2.2.1]HEPTYL RING SYSTEM .I. SYNTHESIS AND CHARACTERIZATION OF SOME 5-SUBSTITUTED DERIVATIVES [J].

ALLRED, EL ;

ANDERSON, CL ;

SMITH, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (11) :3493-&

[3] Electrophilic amination of racemic and non-racemic allenyltitaniums.: One-pot synthesis of α-hydrazinoalkynes from propargylic alcohol derivatives [J].

An, DK ;

Hirakawa, K ;

Okamoto, S ;

Sato, F .

TETRAHEDRON LETTERS, 1999, 40 (19) :3737-3740

[4] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].

Anderson, CE ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413

[5]

BACKVALL JE, 1994, J ORG CHEM, V59, P5850

[6]

Bentz D, 2000, SYNTHESIS-STUTTGART, P1766

[7] ALLYLIC AMINATION BY THE LEWIS-ACID-MEDIATED ENE REACTION OF DIETHYL AZODICARBOXYLATE WITH ALKENES [J].

BRIMBLE, MA ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5261-5263

[8] Enyne metathesis (enyne bond reorganization) [J].

Diver, ST ;

Giessert, AJ .

CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382

[9]

DuBois J, 1997, ANGEW CHEM INT EDIT, V36, P1645

[10] Nitrogen transfer from a nitridomanganese(V) complex: Amination of silyl enol ethers [J].

DuBois, J ;

Hong, J ;

Carreira, EM ;

Day, MW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (04) :915-916

← 1 2 3 4 5 →