Dramatic effect of boron-based Lewis acids in cross-metathesis reactions

被引：52

作者：

Vedrenne, E ^{[1
]}

Dupont, H ^{[1
]}

Oualef, S ^{[1
]}

Elkaïm, L ^{[1
]}

Grimaud, L ^{[1
]}

机构：

[1] Ecole Natl Super Tech Avancees, Lab Chim & Proc, F-75739 Paris, France

来源：

SYNLETT | 2005年 / 04期

关键词：

cross-metathesis; Lewis acid; amino compounds; boron; ruthenium;

D O I：

10.1055/s-2005-862375

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amino compounds such as allylic carbamates or amides are poor partners in cross-metathesis reactions because of possible coordination of the emerging carbene to the polar functional group. Whereas the use of titanium Lewis acid catalysts was unsatisfactory, an impressive increase in yields was obtained with boron-based Lewis acids.

引用

页码：670 / 672

页数：3

共 13 条

[1]

Bentz D, 2000, SYNTHESIS-STUTTGART, P1766

[2] Cross-metathesis of unsaturated α-amino acid derivatives [J].

Biagini, SCG ;

Gibson, SE ;

Keen, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16) :2485-2499

[3] Synthesis of psudoheliotridane via formal [3+2] annulation and ring-closing metathesis [J].

Chang, MY ;

Hsu, RT ;

Tseng, TW ;

Sun, PP ;

Chang, NC .

TETRAHEDRON, 2004, 60 (26) :5545-5550

[4] Recent developments in olefin cross-metathesis [J].

Connon, SJ ;

Blechert, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923

[5] Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond formations [J].

Furstner, A ;

Langemann, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) :9130-9136

[6] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[7] Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex [J].

Gessler, S ;

Randl, S ;

Blechert, S .

TETRAHEDRON LETTERS, 2000, 41 (51) :9973-9976

[8] 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

[9] Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands [J].

Scholl, M ;

Ding, S ;

Lee, CW ;

Grubbs, RH .

ORGANIC LETTERS, 1999, 1 (06) :953-956

[10] A SERIES OF WELL-DEFINED METATHESIS CATALYSTS - SYNTHESIS OF [RUCL2(=CHR')(PR(3))(2)] AND ITS REACTIONS [J].

SCHWAB, P ;

FRANCE, MB ;

ZILLER, JW ;

GRUBBS, RH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (18) :2039-2041

← 1 2 →