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 [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[3] OXYPHOSPHORANES WITH AN OXAPHOSPHOLENE RING - ANALYSIS OF THE ACTIVATION BARRIERS OF THE ISOMERIZATION PROCESS [J].

BUONO, G ;

LLINAS, JR .

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 [J].

Dudding, Travis ;

Kwon, Ohyun ;

Mercier, Evan .

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 [J].

Fürmeier, S ;

Lau, MML ;

Jie, MSFLK ;

Lützen, A ;

Metzger, JO .

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 [J].

GILLESPIE, P ;

RAMIREZ, F ;

UGI, I ;

MARQUARDING, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1973, 12 (02) :91-119

[9] NUCLEAR MAGNETIC RESONANCE EVIDENCE FOR PATHWAYS OF PSEUDOROTATION IN ALKYLOXYPHOSPHORANES [J].

GORENSTEIN, D ;

WESTHEIMER, FH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :634-+

[10]

HUDSON HR, 1991, HDB PHOSPHORUS, V31, P181

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