Highly Efficient and Enantioselective α-Arylation of Cycloalkanones by Scandium-Catalyzed Diazoalkane-Carbonyl Homologation

被引：24

作者：

Rendina, Victor L. ^{[1
]}

Kaplan, Hilan Z. ^{[1
]}

Kingsbury, Jason S. ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 05期

关键词：

diazo compounds; scandium; asymmetric catalysis; ring expansion; arylation; SILYL ENOL ETHERS; BRONSTED ACID; ASYMMETRIC EPOXIDATION; ALLYLIC ALKYLATION; PROTONATION; KETONES; ALLYLATION; LITHIUM; ACCESS; CYCLOPENTANONES;

D O I：

10.1055/s-0031-1289650

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized alpha-tertiary and -quaternary 2-arylcycloalkanones are rapidly accessed by scandium(III) triflate-catalyzed diazoalkane-carbonyl homologations. Recent developments have allowed for carbon insertion reactions to be performed with catalyst loadings as low as 0.5 mol% on scales up to 5 mmol. Pairing readily available bis- and tris(oxazoline) based ligands with scandium triflate allows access to arylated medium ring carbocycles with enantioselectivities up to 98: 2 er and > 98% yield. The formal C-C insertion of aryldiazomethanes into unsubstituted cycloalkanones provides a single-step solution to the ongoing challenge of alpha-arylation.

引用

页码：686 / 693

页数：8

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