P(RNCH2CH2)3N:: Efficient 1,4-addition catalysts

被引：91

作者：

Kisanga, PB ^{[1
]}

Ilankumaran, P ^{[1
]}

Fetterly, BM ^{[1
]}

Verkade, JG ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 11期

关键词：

D O I：

10.1021/jo010228k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,4-addition of primary alcohols, higher nitroalkanes, and a Schiff's base of an alpha-amino ester to alpha,beta-unsaturated substrates produces the corresponding products in moderate to excellent yields when carried out at -63 to 70 degreesC in the presence of catalytic amounts of the nonionic strong bases P(RNCH2CH2)(3)N (R = Me, i-Pr, i-Bu) in isobutyronitrile. Diastereoselectivity for the anti form of the product is high in the case of the Schiff's base in the absence of lithium ion. These catalysts are easily removed from the product by either column filtration through silica gel or via aqueous workup.

引用

页码：3555 / 3560

页数：6

共 27 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] Amberlyst A-27, an efficient heterogeneous catalyst for the Michael reaction of nitroalkanes with beta-substituted alkene acceptors
Ballini, R
Marziali, P
Mozzicafreddo, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 3209 - 3211
[3] The Michael reaction of nitroalkanes with conjugated enones in aqueous media
Ballini, R
Bosica, G
[J]. TETRAHEDRON LETTERS, 1996, 37 (44) : 8027 - 8030
[4] STEREOSPECIFIC ALKYLATION OF THE SCHIFF-BASE ESTER OF ALANINE WITH 2-SUBSTITUTED-(E)-VINYL AND 2-SUBSTITUTED-(Z)-VINYL BROMIDES - AN EFFICIENT SYNTHESIS OF 2-METHYL-(E)-3,4-DIDEHYDROGLUTAMIC ACID, A POTENT SUBSTRATE-INDUCED IRREVERSIBLE INHIBITOR OF L-GLUTAMATE-1-DECARBOXYLASE
BEY, P
VEVERT, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (16) : 3249 - 3253
[5] Cerium catalyzed Michael addition of 1,3-dicarbonyl compounds under microwave irradiation
Boruah, A
Baruah, M
Prajapati, D
Sandhu, JS
[J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (04) : 653 - 658
[6] BRYCE MR, 1989, J CHEM RES SYNOP, V1, P1
[7] Direct synthesis of α,β-unsaturated nitriles catalyzed by nonionic superbases
D'Sa, BA
Kisanga, P
Verkade, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) : 3961 - 3967
[8] RESOLUTION AND USE IN ALPHA-AMINO-ACID SYNTHESIS OF IMIDAZOLIDINONE GLYCINE DERIVATIVES
FITZI, R
SEEBACH, D
[J]. TETRAHEDRON, 1988, 44 (17) : 5277 - 5292
[9] Synthesis of C5-substituted AE-bicyclic analogues of lycoctonine, inuline and methyllycaconitine
Grangier, G
Trigg, WJ
Lewis, T
Rowan, MG
Potter, BVL
Blagbrough, IS
[J]. TETRAHEDRON LETTERS, 1998, 39 (08) : 889 - 892
[10] Hanyuda K, 1997, SYNLETT, P31

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