P(RNCH2CH2)3N-catalyzed 1,2-addition reactions of activated allylic synthons

被引：36

作者：

Kisanga, PB ^{[1
]}

Verkade, JG ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50010 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 02期

关键词：

D O I：

10.1021/jo0106492

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Activated allylic compounds of the type RCH:CHCH(2)Z (Z = CN, CO2Me) react efficiently with aromatic aldehydes in the presence of 20-40 mol % of P(R'NCH2CH2)(3)N at -94 to -63 degreesC. Both R = H and R = Me lead exclusively to a-addition products. When R = H and Z = CN, an allylic transposition occurs to afford a Baylis-Hillman product as the only product.

引用

页码：426 / 430

页数：5

共 50 条

[31] Bronsted base-catalyzed 1,2-addition/[1,2]-phospha-Brook rearrangement sequence providing functionalized phosphonates
Kondoh, Azusa
Terada, Masahiro
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (14) : 2863 - 2866
[32] Free and polymer-bound tricyclic azaphosphatranes HP(RNCH2CH2)3N+:: Procatalysts in dehydrohalogenations and debrominations with NaH (vol 64, pg 4840, 1999)
Liu, XD
Verkade, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21): : 8058 - 8058
[33] PHOTOCHEMICAL REACTIONS OF DIKETONES .2. 1,2-ADDITION OF SUBSTITUTED TOLUENES TO 9,10-PHENANTHRENEQUINONE
RUBIN, MB
ZWITKOWI.P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (08): : 2362 - &
[34] 1,2-Addition of Formic or Oxalic Acid to -N{CH2CH2(PiPr2)}2-Supported Mn(I) Dicarbonyl Complexes and the Manganese-Mediated Decomposition of Formic Acid
Tondreau, Aaron M.
Boncella, James M.
[J]. ORGANOMETALLICS, 2016, 35 (12) : 2049 - 2052
[35] Synthesis of Ar-BINMOL Ligands by [1,2]-Wittig Rearrangement to Probe Their Catalytic Activity in 1,2-Addition Reactions of Aldehydes with Grignard Reagents
Zheng, Long-Sheng
Jiang, Ke-Zhi
Deng, Yuan
Bai, Xing-Feng
Gao, Guang
Gu, Feng-Lei
Xu, Li-Wen
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (04) : 748 - 755
[36] Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates
Weischedel, Heike
Schmidt, Dietmar
Conrad, Juergen
Beifuss, Uwe
[J]. TETRAHEDRON, 2018, 74 (44) : 6426 - 6441
[37] Ethanol oxidation reactions catalyzed by water molecules:: CH3CH2OH+nH2O→CH3CHO+H2+nH2O (n = 0, 1, 2)
Takahashi, H
Hisaoka, S
Nitta, T
[J]. CHEMICAL PHYSICS LETTERS, 2002, 363 (1-2) : 80 - 86
[38] Synthesis, characterization and reactions of [RhCl(CO){(Ph2P(CH2CH2O)m CH2CH2Ph2-P,P′)}]n (m=3, 4, 5 n=1, 2...) metallacrown crown ethers
Smith, Dale C.
Cagle, Ethan C.
Gray, Gary M.
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 876 : 78 - 82
[39] Merrifield resin-C6H4CH2N3P(MeNCH2CH2)3N:: An efficient reusable catalyst for room-temperature 1,4-addition reactions and a more convenient synthesis of its precursor P(MeNCH2CH2)3N
Reddy, Chinta
Reddy, Venkat
Verkade, John G.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08): : 3093 - 3096
[40] Aryne-Induced Novel Tandem 1,2-Addition/(3+2) Cycloaddition to Generate Imidazolidines and Pyrrolidines
Swain, Sharada P.
Shih, Yi-Chun
Tsay, Shwu-Chen
Jacob, Joby
Lin, Chun-Cheng
Hwang, Kuo Chu
Horng, Jia-Cherng
Hwu, Jih Ru
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) : 9926 - 9930

← 1 2 3 4 5 →