Ruthenium-catalyzed cross-metathesis between diallylsilanes and electron-deficient Olefins

被引：17

作者：

BouzBouz, Samir ^{[1
]}

Boulard, Lucie ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI, CNRS, Chim Organ Lab, F-75231 Paris 5, France

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 19期

关键词：

D O I：

10.1021/ol0712632

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diallysilanes can be selectively coupled with electron-deficient olefins under cross-metathesis (CM) conditions using the Hoveyda-Grubbs catalyst to produce mono- and/or bis-CM compounds in good yield. The formation of the mono- and the bis-CM compounds depends on the nature of the electron-deficient olefin.

引用

页码：3765 / 3768

页数：4

共 26 条

[11] Recent advances in olefin metathesis and its application in organic synthesis [J].

Grubbs, RH ;

Chang, S .

TETRAHEDRON, 1998, 54 (18) :4413-4450

[12] Highly diastereo- and enantioselective reagents for aldehyde crotylation [J].

Hackman, BM ;

Lombardi, PJ ;

Leighton, JL .

ORGANIC LETTERS, 2004, 6 (23) :4375-4377

[13] Olefin metathesis-active ruthenium complexes bearing a nucleophilic carbene ligand [J].

Huang, JK ;

Stevens, ED ;

Nolan, SP ;

Petersen, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) :2674-2678

[14] HYDROLYSIS OF SOME CYCLIC ESTERS OF SULFURIC ACID [J].

KAISER, ET ;

PANAR, M ;

WESTHEIMER, FH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (05) :602-&

[15] A recyclable Ru-based metathesis catalyst [J].

Kingsbury, JS ;

Harrity, JPA ;

Bonitatebus, PJ ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :791-799

[16] Synthesis and [4+2]-annulation of enantioenriched (Z)-crotylsilanes:: Preparation of the C1-C13 fragment of bistramide A [J].

Lowe, JT ;

Panek, JS .

ORGANIC LETTERS, 2005, 7 (15) :3231-3234

[17] Stereocontrolled [4+2]-annulation accessing dihydropyrans: Synthesis of the C1a-C10 fragment of kendomycin [J].

Lowe, JT ;

Panek, JS .

ORGANIC LETTERS, 2005, 7 (08) :1529-1532

[18] Reagent-controlled stereoselective synthesis of lignan-related tetrahydrofurans [J].

Miles, SM ;

Marsden, SP ;

Leatherbarrow, RJ ;

Coates, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6874-6882

[19] DIRECTED DILITHIATION OF HEXAFLUOROCUMYL ALCOHOL - FORMATION OF A REAGENT FOR THE FACILE INTRODUCTION OF A STABILIZING BIDENTATE LIGAND IN COMPOUNDS OF HYPERVALENT SULFUR (10-S-4), PHOSPHORUS (10-P-5), SILICON (10-SI-5), AND IODINE (10-I-3) [J].

PEROZZI, EF ;

MICHALAK, RS ;

FIGULY, GD ;

STEVENSON, WH ;

DESS, DB ;

ROSS, MR ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1049-1053

[20]

Phillips AJ, 1999, ALDRICHIM ACTA, V32, P75

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