Lanthanide Lewis acid-mediated enantioselective conjugate radical additions

被引：37

作者：

Sibi, MP ^{[1
]}

Manyem, S ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem, Fargo, ND 58105 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 17期

关键词：

D O I：

10.1021/ol026327h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lanthanide triflates along with proline-derived ligands have been found to be efficient catalysts for enantioselective conjugate addition of nucleophilic radicals to enoates. N-Acyl oxazolidinones, when used as achiral additives, gave meaningful enhancements in the ees for the product.

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页码：2929 / 2932

页数：4

相关论文

共 55 条

[1] Chiral lanthanide complexes: Coordination chemistry and applications [J].

Aspinall, HC .

CHEMICAL REVIEWS, 2002, 102 (06) :1807-1850

[2] Defining effective chiral binding sites at lanthanides - highly enantioselective reagents and catalysts from binaphtholate and pybox ligands [J].

Aspinall, HC ;

Greeves, N .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 647 (1-2) :151-157

[3] Lanthanum triflate-catalysed allylation of aldehydes: crucial activation by benzoic acid [J].

Aspinall, HC ;

Bissett, JS ;

Greeves, N ;

Levin, D .

TETRAHEDRON LETTERS, 2002, 43 (02) :319-321

[4] Solubilized lanthanide triflates:: Lewis acid catalysis by polyether and poly(ethylene glycol) complexes of Ln(OTf)3 [J].

Aspinall, HC ;

Dwyer, JLM ;

Greeves, N ;

McIver, EG ;

Woolley, JC .

ORGANOMETALLICS, 1998, 17 (09) :1884-1888

[5] A CHIRAL SAMARIUM-BASED CATALYST FOR THE ASYMMETRIC MEERWEIN-PONNDORF-VERLEY REDUCTION [J].

EVANS, DA ;

NELSON, SG ;

GAGNE, MR ;

MUCI, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9800-9801

[6] Enantioselective radical allylation of alpha-iodoamides using chiral aluminum based Lewis acids [J].

Fhal, AR ;

Renaud, P .

TETRAHEDRON LETTERS, 1997, 38 (15) :2661-2664

[7]

Fukuzawa S, 2001, SYNLETT, P709

[8] A facile synthesis of chiral gamma-butyrolactones in extremely high enantioselectivity mediated by samarium(II) iodide [J].

Fukuzawa, S ;

Seki, K ;

Tatsuzawa, M ;

Mutoh, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) :1482-1483

[9]

Giese B., 1986, RADICALS ORGANIC SYN

[10] Positive cooperativity of product mimics in the asymmetric autoinduction of Diels-Alder reactions catalyzed by a VAPOL-aluminum catalyst [J].

Heller, DP ;

Goldberg, DR ;

Wulff, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) :10551-10552

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