Synthesis of highly functionalized alkenylphosphines by Lewis acid-mediated silylphosphination of substituted propiolates

被引：16

作者：

Hayashi, Minoru ^{[1
]}

Matsuura, Yutaka ^{[1
]}

Kurihara, Katsutoshi ^{[1
]}

Maeda, Daisuke ^{[1
]}

Nishimura, Yasunobu ^{[1
]}

Morita, Emi ^{[1
]}

Okasaka, Miho ^{[1
]}

机构：

[1] Ehime Univ, Grad Sch Sci & Engn, Dept Mat Sci & Biotechnol, Matsuyama, Ehime 7908577, Japan

来源：

CHEMISTRY LETTERS | 2007年 / 36卷 / 05期

关键词：

D O I：

10.1246/cl.2007.634

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A synthesis of highly substituted alkenylphosphines by Lewis acid-mediated silylphosphination of substituted propiolates is described. The addition proceeded smoothly to give the corresponding acrylates, where the phosphino group attached at the beta and the silyl group located at the alpha position of the resulting acrylate, in exclusively syn-stereochemistry.

引用

页码：634 / 635

页数：2

共 12 条

[1] Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes [J].

Beletskaya, Irina ;

Moberg, Christina .

CHEMICAL REVIEWS, 2006, 106 (06) :2320-2354

[2] SOME REACTIONS OF HEXAFLUOROBUTYNE-2 WITH PHOSPHINES AND AMINES [J].

CULLEN, WR ;

DAWSON, DS .

CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (23) :2887-&

[3] Stereospecific diphosphination of activated acetylenes: A general route to backbone-functionalized, chelating 1,2-diphosphinoethenes [J].

Dodds, Deborah L. ;

Haddow, Mairi F. ;

Orpen, A. Guy ;

Pringle, Paul G. ;

Woodward, Gary .

ORGANOMETALLICS, 2006, 25 (25) :5937-5945

[4]

Haber S, 1999, CHEM-EUR J, V5, P1581, DOI 10.1002/(SICI)1521-3765(19990503)5:5<1581::AID-CHEM1581>3.0.CO

[5]

2-2

[6] Fluoride-catalyzed three-component coupling reaction of a silylphosphine, activated alkenes and aldehydes [J].

Hayashi, M ;

Matsuura, Y ;

Watanabe, Y .

TETRAHEDRON LETTERS, 2005, 46 (31) :5135-5138

[7] Fluoride-mediated phosphination of alkenes and alkynes by silylphosphines [J].

Hayashi, M ;

Matsuura, Y ;

Watanabe, Y .

TETRAHEDRON LETTERS, 2004, 45 (50) :9167-9169

[8] Regio- and stereoselective synthesis of alkenylphosphines: A rhodium-catalyzed hydrophosphination of alkynes using a silylphosphine [J].

Hayashi, Minoru ;

Matsuura, Yutaka ;

Watanabe, Yutaka .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :9248-9251

[9]

Miyashita N., 2001, Chemical-Mechanical Polishing 2000 - Fundamentals and Materials Issues. Symposium (Materials Research Society Symposium Proceedings Vol.613), P1, DOI 10.1002/3527600159.ch1

[10]

Reisser M, 2002, SYNLETT, P1459

← 1 2 →