Stable tetravalent phosphonium enolate zwitterions

被引：141

作者：

Zhu, Xue-Feng ^{[1
]}

Henry, Christopher E. ^{[1
]}

Kwon, Ohyun ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 21期

关键词：

D O I：

10.1021/ja071990s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three-component coupling reactions between trialkylphosphines, methyl propiolates, and aldehydes produced 1:1:1 dipolar adducts in moderate to excellent yields. The product phosphonium enolate zwitterions were isolated as crystalline solids. X-ray crystallographic analyses of these single crystals established unequivocally the dipolar structures of these tetravalent phosphonium enolate zwitterions. Because phosphonium enolates are the first key intermediates in the nucleophilic phosphine-mediated catalysis of alpha,beta-unsaturated carbonyl compounds, this study provides crucial insight into the mechanisms of Morita-Baylis-Hillman-type reactions.

引用

页码：6722 / +

页数：3

共 33 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS
ALLEN, FH
KENNARD, O
WATSON, DG
BRAMMER, L
ORPEN, AG
TAYLOR, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12): : S1 - S19
[2] Recent advances in the Baylis-Hillman reaction and applications
Basavaiah, D
Rao, AJ
Satyanarayana, T
[J]. CHEMICAL REVIEWS, 2003, 103 (03) : 811 - 891
[3] OXYPHOSPHORANES WITH AN OXAPHOSPHOLENE RING - ANALYSIS OF THE ACTIVATION BARRIERS OF THE ISOMERIZATION PROCESS
BUONO, G
LLINAS, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) : 4532 - 4540
[4] BUONO G, 1972, TETRAHEDRON LETT, V13, P149
[5] Ciganek E., 1997, ORG REACTIONS, V51, P201
[6] Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes
Dudding, Travis
Kwon, Ohyun
Mercier, Evan
[J]. ORGANIC LETTERS, 2006, 8 (17) : 3643 - 3646
[7] Expanding the field of phosphorus-containing fatty acid derivatives:: Synthesis of 1,2-oxaphospholene derivatives and alkenyl phosphonates from α-keto allenes
Fürmeier, S
Lau, MML
Jie, MSFLK
Lützen, A
Metzger, JO
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) : 4874 - 4878
[8] CHEMISTRY AND LOGICAL STRUCTURES .5. DISPLACEMENT REACTIONS OF PHOSPHORUS(V) COMPOUNDS AND THEIR PENTACOORDINATE INTERMEDIATES
GILLESPIE, P
RAMIREZ, F
UGI, I
MARQUARDING, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1973, 12 (02) : 91 - 119
[9] NUCLEAR MAGNETIC RESONANCE EVIDENCE FOR PATHWAYS OF PSEUDOROTATION IN ALKYLOXYPHOSPHORANES
GORENSTEIN, D
WESTHEIMER, FH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) : 634 - +
[10] HUDSON HR, 1991, HDB PHOSPHORUS, V31, P181

← 1 2 3 4 →