P(RNCH2CH2)3N:: An efficient promoter for the nitroaldol (Henry) reaction

被引：105

作者：

Kisanga, PB ^{[1
]}

Verkade, JG ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 12期

关键词：

D O I：

10.1021/jo9818733

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of catalytic amounts of the proazaphosphatranes P(MeNCH2CH2)(3)N, P(i-PrNCH2CH2)(3)N and P(HNCH2CN2)(i-PrNCH2CH2)(2)N as nonionic bases in the reaction of nitroalkanes with carbonyl compounds is reported. The reaction proceeds at room temperature in the presence of 2.2 equiv of magnesium sulfate to produce the corresponding beta-nitroalkanols in generally superior yields. Aldehydes react quantitatively in 5-60 min, whereas ketones require up to 3 h to react with nitromethane and up to 7 h for the reaction of ketones with higher nitroalkanes.

引用

页码：4298 / 4303

页数：6

共 33 条

[1] P(CH3NCH2CH2)(3)N: A nonionic superbase for efficient dehydrohalogenation
Arumugam, S
Verkade, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) : 4827 - 4828
[2] NEW AND CONVENIENT SYNTHESIS OF (Z)-HENEICOS-6-EN-11-ONE, THE DOUGLAS-FIR TUSSOCK MOTH (ORGYIA-PSEUDOTSUGATA) SEX-PHEROMONE, AND (Z)-NON-6-EN-2-ONE, THE IMMEDIATE PRECURSOR FOR THE SYNTHESIS OF BREVICOMIN, THE SEX ATTRACTANT OF THE WESTERN PINE-BEETLE DENTROCTONUS-BREVICOMIS
BALLINI, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06): : 1419 - 1421
[3] Nitroaldol (Henry) reaction catalyzed by Amberlyst A-21 as a far superior heterogeneous catalyst.
Ballini, R
Bosica, G
Forconi, P
[J]. TETRAHEDRON, 1996, 52 (05) : 1677 - 1684
[4] BALLINI R, 1993, J CHEM RES-S, P371
[5] A NEW STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA,BETA-UNSATURATED-GAMMA-DICARBONYL COMPOUNDS BY THE HENRY REACTION
BALLINI, R
BOSICA, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) : 5466 - 5467
[6] Enantiodivergent synthesis of 2-hydroxymethyl-3-hydroxy-4-nitro-pyrrolidines through tandem Michael-Henry reaction using L-serine as the chiral educt.
Barco, A
Benetti, S
DeRisi, C
Pollini, GP
Romagnoli, R
Zanirato, V
[J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7599 - 7602
[7] BRITTAIN R, 1970, ADV DRUG RES, P5
[8] Nonionic superbase-catalyzed silylation of alcohols. (vol 62, pg 5058, 1997)
D'Sa, B
McLeod, D
Verkade, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) : 9144 - 9144
[9] Synthesis of a novel exceedingly strong nonionic superbase
D'Sa, BA
Verkade, JG
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 123 : 301 - 312
[10] TOTAL SYNTHESIS OF BIOLOGICALLY IMPORTANT AMINO-SUGARS VIA THE NITROALDOL REACTION
HANESSIAN, S
KLOSS, J
[J]. TETRAHEDRON LETTERS, 1985, 26 (10) : 1261 - 1264

← 1 2 3 4 →