Selective hydroformylation of N-allylacetamide in an inverted aqueous two-phase catalytic system, enabling a short synthesis of melatonin

被引：39

作者：

Verspui, G ^{[1
]}

Elbertse, G ^{[1
]}

Sheldon, FA ^{[1
]}

Hacking, MAPJ ^{[1
]}

Sheldon, RA ^{[1
]}

机构：

[1] Delft Univ Technol, Organ Chem & Catalysis Lab, NL-2628 BL Delft, Netherlands

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 15期

关键词：

D O I：

10.1039/b003715j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Water increases the selectivity in the Rh-phosphine catalysed hydroformylation of N-allylacetamide; an aqueous-organic biphasic system, containing a hydrophobic Rh-catalyst, provided facile catalyst/product separation, after which the aqueous product phase could be used in a one-pot synthesis of N-acetyl-5-methoxytryptamine (melatonin).

引用

页码：1363 / 1364

页数：2

共 21 条

[1] ASYMMETRIC HYDROFORMYLATION AND HYDROCARBOXYLATION OF ENAMIDES - SYNTHESIS OF ALANINE AND PROLINE [J].

BECKER, Y ;

EISENSTADT, A ;

STILLE, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2145-2151

[2] ADVANCES IN THE HYDROFORMYLATION OF OLEFINS CONTAINING FUNCTIONAL-GROUPS [J].

BOTTEGHI, C ;

GANZERLA, R ;

LENARDA, M ;

MORETTI, G .

JOURNAL OF MOLECULAR CATALYSIS, 1987, 40 (02) :129-182

[3]

Chauvin Y, 1995, ANGEW CHEM INT EDIT, V34, P2698

[4] PRACTICAL, HIGH-YIELD, REGIOSELECTIVE, RHODIUM-CATALYZED HYDROFORMYLATION OF FUNCTIONALIZED ALPHA-OLEFINS [J].

CUNY, GD ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (05) :2066-2068

[5] Tandem reaction sequences under hydroformylation conditions:: New synthetic applications of transition metal catalysis [J].

Eilbracht, P ;

Bärfacker, L ;

Buss, C ;

Hollmann, C ;

Kitsos-Rzychon, BE ;

Kranemann, CL ;

Rische, T ;

Roggenbuck, R ;

Schmidt, A .

CHEMICAL REVIEWS, 1999, 99 (11) :3329-3365

[6] ENHANCEMENT OF CATALYTIC ACTIVITY FOR HYDROFORMYLATION OF METHYL ACRYLATE BY USING BIPHASIC AND SUPPORTED AQUEOUS-PHASE SYSTEMS [J].

FREMY, G ;

MONFLIER, E ;

CARPENTER, JF ;

CASTANET, Y ;

MORTREUX, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (13-14) :1474-1476

[7] Molecular engineering in homogeneous catalysis:: One-phase catalysis coupled with biphase catalyst separation.: The fluorous-soluble HRh(CO){P[CH2CH2(CF2)5CF3]3}3 hydroformylation system [J].

Horváth, IT ;

Kiss, G ;

Cook, RA ;

Bond, JE ;

Stevens, PA ;

Rábai, J ;

Mozeleski, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3133-3143

[8]

HUGEL HM, 1995, ORG PREP PROCED INT, V27, P1

[9] NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE [J].

KRANENBURG, M ;

VANDERBURGT, YEM ;

KAMER, PCJ ;

VANLEEUWEN, PWNM ;

GOUBITZ, K ;

FRAANJE, J .

ORGANOMETALLICS, 1995, 14 (06) :3081-3089

[10]

KUNTZ EG, 1987, CHEMTECH, V17, P570

← 1 2 3 →