Enantioselective Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones

被引：75

作者：

Blay, Gonzalo ^{[1
]}

Fernandez, Isabel ^{[1
]}

Monleon, Alicia ^{[1
]}

Pedro, Jose R. ^{[1
]}

Vila, Carlos ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Valencia, Spain

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

NUCLEOPHILIC TRIFLUOROMETHYLATION; ASYMMETRIC-SYNTHESIS; HENRY REACTION; CONSTRUCTION; FLUORINE; REAGENTS; BINOL; FLUOROMETHYL; PHENYLATION; DERIVATIVES;

D O I：

10.1021/ol802509m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic enantioselective Friedel-Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones to give pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety bearing a quaternary stereogenic center is described. The reaction is achieved in the presence of a 3,3'dibromo-BINOL-Zr(IV) complex to give the expected products with high yields (up to 98%) and good enantioselectivities (up to 93% ee). The absolute stereochemistry of the products has been determined by chemical correlation.

引用

页码：441 / 444

页数：4

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