Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones

被引：51

作者：

Bolm, C ^{[1
]}

Beckmann, O ^{[1
]}

Palazzi, C ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2001年 / 79卷 / 11期

关键词：

aluminum; asymmetric catalysis; lactones; oxidations; rearrangement;

D O I：

10.1139/cjc-79-11-1593

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

BINOL-aluminum complexes were successfully employed as mediators and catalysts in asymmetric Baeyer-Villiger rearrangements of cyclobutanones. Good enantioselectivies were achieved with only 15 mol% of the chosen chiral Lewis acid. The enantiomeric excesses obtained have never been reached before in such metal-catalyzed Baeyer-Villiger reactions.

引用

页码：1593 / 1597

页数：5

共 80 条

[71]

1716::AID-ANGE1716ANDGT

[72]

3.0.CO

[73]

2-D]

[74] Synthesis and Absolute Configuration of (-)-meridinol and (-)-3-epimeridinol [J].

Takano, D ;

Doe, M ;

Morimoto, Y ;

Yoshihara, K ;

Kinoshita, T .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (01) :221-224

[75] Rhodium-catalyzed asymmetric 1,4-addition of arylboron reagents to α,β-unsaturated esters [J].

Takaya, Y ;

Senda, T ;

Kurushima, H ;

Ogasawara, M ;

Hayashi, T .

TETRAHEDRON-ASYMMETRY, 1999, 10 (20) :4047-4056

[76] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE GLYOXYLATE-ENE REACTION CATALYZED BY NEW CLASS OF BINAPHTHOL-DERIVED TITANIUM COMPLEX [J].

TERADA, M ;

MOTOYAMA, Y ;

MIKAMI, K .

TETRAHEDRON LETTERS, 1994, 35 (36) :6693-6696

[77] Ruthenium-catalyzed cycloisomerization-oxidation of homopropargyl alcohols.: A new access to γ-butyrolactones [J].

Trost, BM ;

Rhee, YH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (50) :11680-11683

[78] LEWIS ACID-ENHANCED REACTIVITY OF ALPHA,BETA-UNSATURATED ESTER AND AMIDE TOWARD RADICAL-ADDITION [J].

URABE, H ;

YAMASHITA, K ;

SUZUKI, K ;

KOBAYASHI, K ;

SATO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3576-3577

[79] ASYMMETRIC-SYNTHESIS OF LIGNANS [J].

WARD, RS .

TETRAHEDRON, 1990, 46 (15) :5029-5041

[80] Chiral Mo-binol complexes: Activity, synthesis, and structure. Efficient enantioselective six-membered ring synthesis through catalytic metathesis [J].

Zhu, SS ;

Cefalo, DR ;

La, DS ;

Jamieson, JY ;

Davis, WM ;

Hoveyda, AH ;

Schrock, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (36) :8251-8259

← 1 2 3 4 5 6 7 8 →