Efficient and practical Ag-catalyzed cycloadditions between arylimines and the Danishefsky diene

被引：151

作者：

Josephsohn, NS ^{[1
]}

Snapper, ML ^{[1
]}

Hoveyda, AH ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 14期

关键词：

D O I：

10.1021/ja030033p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient Ag-catalyzed method for asymmetric addition of the Danishefsky diene to various aryl imines to afford cycloadducts in ≥89% ee and ≥85% isolated yield is reported. Reactions are effected with 0.1-1 mol % catalyst (4 °C), and the chiral ligand is readily prepared from commercially available materials, including the inexpensive i-Leu. These catalytic asymmetric cycloadditions can be carried out without the use of solvent or with undistilled THF in air. A first generation supported chiral catalyst that effectively promotes the cycloaddition reaction and can be recycled (five cycles) is described. Copyright © 2003 American Chemical Society.

引用

页码：4018 / 4019

页数：2

共 27 条

[1]

BHATTARAI K, 1990, SYNLETT, P229

[2] Discovery of chiral catalysts through ligand diversity: Ti-catalyzed enantioselective addition of TMSCN to meso epoxides [J].

Cole, BM ;

Shimizu, KD ;

Krueger, CA ;

Harrity, JPA ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1668-1671

[3] Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric syntheses of indolizidine alkaloids (-)-205A, (-)-207A, and (-)-235B [J].

Comins, DL ;

LaMunyon, DH ;

Chen, XH .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8182-8187

[4] TOTALLY SYNTHETIC ROUTES TO THE HIGHER MONOSACCHARIDES [J].

DANISHEFSKY, SJ ;

DENINNO, MP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :15-23

[5] Efficient cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones [J].

Degrado, SJ ;

Mizutani, H ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13362-13363

[6] Modular peptide-based phosphine ligands-in asymmetric catalysis: Efficient and enantioselective Cu-catalyzed conjugate additions to five-, six-, and seven-membered cyclic enones [J].

Degrado, SJ ;

Mizutani, H ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :755-756

[7] Asymmetric catalysis with libraries of palladium β-turn phosphine complexes [J].

Gilbertson, SR ;

Collibee, SE ;

Agarkov, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) :6522-6523

[8] ASYMMETRIC AZA-DIELS-ALDER REACTION MEDIATED BY CHIRAL BORON REAGENT [J].

HATTORI, K ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3264-3265

[9]

HIRD AW, IN PRESS ANGEW CHEM

[10]

HOVEYDA AH, 2002, HDB COMBINATORIAL CH, P991

← 1 2 3 →